CN119661543A - Preparation method of 2-Boc-2, 7-diaza-spiro [4.4] nonane - Google Patents
Preparation method of 2-Boc-2, 7-diaza-spiro [4.4] nonane Download PDFInfo
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- CN119661543A CN119661543A CN202411832664.4A CN202411832664A CN119661543A CN 119661543 A CN119661543 A CN 119661543A CN 202411832664 A CN202411832664 A CN 202411832664A CN 119661543 A CN119661543 A CN 119661543A
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- nonane
- spiro
- boc
- diazaspiro
- dione
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- HPPARSNAMZJAPZ-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.4]nonane-2-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC11CNCC1 HPPARSNAMZJAPZ-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title description 5
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000011630 iodine Substances 0.000 claims abstract description 9
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 9
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 9
- 239000002608 ionic liquid Substances 0.000 claims abstract description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- -1 spiro[3.3]heptane-2,6-dione dioxime Chemical compound 0.000 claims description 12
- GLUGRUJRPBFVMF-UHFFFAOYSA-N 2,7-diazaspiro[4.4]nonane-3,8-dione Chemical compound C1NC(=O)CC21CC(=O)NC2 GLUGRUJRPBFVMF-UHFFFAOYSA-N 0.000 claims description 11
- 238000010992 reflux Methods 0.000 claims description 7
- SPMIAKLTMJWZDX-UHFFFAOYSA-N spiro[3.3]heptane-2,6-dione Chemical compound C1C(=O)CC21CC(=O)C2 SPMIAKLTMJWZDX-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- UBIJTWDKTYCPMQ-UHFFFAOYSA-N hexachlorophosphazene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 UBIJTWDKTYCPMQ-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
- 239000001632 sodium acetate Substances 0.000 claims description 3
- 235000017281 sodium acetate Nutrition 0.000 claims description 3
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical group ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 claims 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims 1
- DDVRNOMZDQTUNS-UHFFFAOYSA-N 2,7-diazaspiro[4.4]nonane Chemical compound C1NCCC11CNCC1 DDVRNOMZDQTUNS-UHFFFAOYSA-N 0.000 abstract description 7
- OQHQOOLVQDEIGL-UHFFFAOYSA-N 2-methyl-2,7-diazaspiro[4.4]nonane Chemical compound C1N(C)CCC11CNCC1 OQHQOOLVQDEIGL-UHFFFAOYSA-N 0.000 abstract description 5
- 125000003003 spiro group Chemical group 0.000 abstract description 5
- 238000006237 Beckmann rearrangement reaction Methods 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 3
- 230000009471 action Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000012043 crude product Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- AQFPAMFDGCIZAY-UHFFFAOYSA-K C(CCC)N1CN(C=C1)C.[Al](Cl)(Cl)Cl Chemical compound C(CCC)N1CN(C=C1)C.[Al](Cl)(Cl)Cl AQFPAMFDGCIZAY-UHFFFAOYSA-K 0.000 description 2
- 229910010082 LiAlH Inorganic materials 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- IAJDKRFEVXVEEC-UHFFFAOYSA-L [Cl-].[Zn+2].C(CCC)N1CN(C=C1)C.[Cl-] Chemical compound [Cl-].[Zn+2].C(CCC)N1CN(C=C1)C.[Cl-] IAJDKRFEVXVEEC-UHFFFAOYSA-L 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- ATCRXJYHZSNQFI-UHFFFAOYSA-N diethyl 3,3-dicyanopentanedioate Chemical compound CCOC(=O)CC(C#N)(C#N)CC(=O)OCC ATCRXJYHZSNQFI-UHFFFAOYSA-N 0.000 description 1
- OUWSNHWQZPEFEX-UHFFFAOYSA-N diethyl glutarate Chemical compound CCOC(=O)CCCC(=O)OCC OUWSNHWQZPEFEX-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000006362 organocatalysis Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
本发明公开了一种2‑Boc‑2,7‑二氮杂‑螺[4.4]壬烷的制备方法，属于有机中间体技术领域。以螺[3.3]庚烷‑2,6‑二酮为原料，与盐酸羟胺反应生成螺[3.3]庚烷‑2,6‑二酮二肟；随后在三氯化铝离子液体和催化剂条件下，进行Beckmann重排，生成2,7‑二氮杂螺[4.4]壬烷‑3,8‑二酮；然后经过硼氢化钠和碘还原，生成2,7‑二氮杂螺[4.4]壬烷；最后与(Boc)2O反应，生成2‑Boc‑2,7‑二氮杂螺[4.4]壬烷。本发明采用螺[3.3]庚烷‑2,6‑二酮二肟在催化剂作用下进行Beckmann重排，构筑出2,7‑二氮杂螺[4.4]壬烷‑3,8‑二酮框架。The invention discloses a method for preparing 2-Boc-2,7-diaza-spiro[4.4]nonane, and belongs to the technical field of organic intermediates. Spiro[3.3]heptane-2,6-diketone is used as a raw material, and hydroxylamine hydrochloride is reacted to generate spiro[3.3]heptane-2,6-diketone dioxime; then, under the conditions of aluminum chloride ionic liquid and catalyst, Beckmann rearrangement is performed to generate 2,7-diazaspiro[4.4]nonane-3,8-diketone; then, sodium borohydride and iodine are reduced to generate 2,7-diazaspiro[4.4]nonane; finally, (Boc) 2 O is reacted to generate 2-Boc-2,7-diazaspiro[4.4]nonane. The present invention adopts spiro[3.3]heptane-2,6-diketone dioxime to perform Beckmann rearrangement under the action of a catalyst to construct a 2,7-diazaspiro[4.4]nonane-3,8-diketone framework.
Description
Technical Field
The invention relates to a preparation method of 2-Boc-2, 7-diaza-spiro [4.4] nonane, and belongs to the technical field of organic intermediates.
Background
2-Boc-2, 7-diazaspiro [4.4] nonane (CAS number: 236406-49-8) is an important organic synthesis intermediate, and has wide application in the fields of medicines, pesticides, photoelectric conversion materials and the like. The 2, 7-diazaspiro [4.4] nonane skeleton is also an important building block in the fields of organocatalysis and metal catalysis.
Concerning the synthesis of 2, 7-diazaspiro [4.4] nonane, there are few reports currently, mainly the following two routes:
A. Patent and literature [ WO200730061A; journal of Organic Chemistry,1981,46,2757] report that 3, 3-dicyano diethyl glutarate is synthesized by using malononitrile and ethyl 2-bromoacetate as raw materials under the condition of sodium hydride, then 2, 7-diazaspiro [4.4] nonane-1, 3,6, 8-tetraketone is generated by reflux reaction under the condition of concentrated sulfuric acid and glacial acetic acid, and then LiAlH 4 is reduced to generate 2, 7-diazaspiro [4.4] nonane.
B. Literature [ Journal ofMedicinal Chemistry,1990,33,2270] reports the synthesis of diethyl 3, 3-dicyanoglutarate from malononitrile and ethyl 2-bromoacetate under sodium hydride conditions, followed by synthesis of 2, 7-diazaspiro [4.4] nonane-3, 8-dione under Raney cobalt and hydrogen conditions, followed by reduction by LiAlH 4 to give 2, 7-diazaspiro [4.4] nonane.
Aiming at the defects of the above routes, the synthesis route of 2-Boc-2, 7-diazaspiro [4.4] nonane needs to be studied in depth, and a better process route with cheap and easily available raw materials is provided to meet the increasing market demands.
Disclosure of Invention
The invention aims to solve the technical problem of providing a preparation method of 2-Boc-2, 7-diazaspiro [4.4] nonane. The method provided by the invention takes spiro [3.3] heptane-2, 6-dione as a raw material, reacts with hydroxylamine hydrochloride to generate spiro [3.3] heptane-2, 6-dione dioxime, then performs Beckmann rearrangement under the conditions of aluminum trichloride ionic liquid and a catalyst to generate 2, 7-diazaspiro [4.4] nonane-3, 8-dione, then reduces with sodium borohydride and iodine to generate 2, 7-diazaspiro [4.4] nonane, and finally reacts with (Boc 2 O to generate 2-Boc-2, 7-diazaspiro [4.4] nonane.
The preparation method of the 2-Boc-2, 7-diazaspiro [4.4] nonane is realized by the following technical scheme, and the reaction equation is expressed as follows:
the method comprises the following steps:
A. Mixing spiro [3.3] heptane-2, 6-dione, hydroxylamine hydrochloride and alkali in methanol, and reacting under reflux condition to obtain spiro [3.3] heptane-2, 6-dione dioxime;
B. Mixing spiro [3.3] heptane-2, 6-diketone dioxime, ionic liquid and catalyst in hexafluoroisopropanol, and reacting under the condition of heating to generate 2, 7-diazaspiro [4.4] nonane-3, 8-diketone;
C. mixing 2, 7-diazaspiro [4.4] nonane-3, 8-dione, sodium borohydride and iodine in THF, reacting under reflux, cooling to room temperature, adding methanol and (Boc) 2 O, and forming 2-Boc-2, 7-diazaspiro [4.4] nonane;
Preferably, in step a of the above technical scheme, the base is selected from sodium acetate or sodium carbonate.
Preferably, in the step A of the technical scheme, the mole ratio of the spiro [3.3] heptane-2, 6-dione, hydroxylamine hydrochloride and the alkali is 1:2-2.5:3-3.5.
Preferably, in the step B of the above technical scheme, the ionic liquid is selected from 1-butyl-3-methylimidazole ferric chloride salt, 1-butyl-3-methylimidazole zinc chloride salt or 1-butyl-3-methylimidazole aluminum chloride salt.
Preferably, in the step B of the above technical scheme, the temperature raising condition is 40-50 ℃.
Preferably, in step B of the above technical scheme, the catalyst is selected from cyanuric chloride or hexachlorocyclotriphosphazene.
Preferably, in the step B of the above technical scheme, the molar ratio of the spiro [3.3] heptane-2, 6-dione dioxime, the ionic liquid and the catalyst is 1:0.01-0.05:0.001-0.003.
Preferably, in step C of the above technical scheme, the molar ratio of the lattice 2, 7-diazaspiro [4.4] nonane-3, 8-dione, sodium borohydride, iodine and (Boc) 2 O is 1:3-3.5:2-3:1-1.1.
The invention has the beneficial effects that
A. the invention adopts spiro [3.3] heptane-2, 6-diketone dioxime to carry out Beckmann rearrangement under the action of a catalyst to construct a 2, 7-diazaspiro [4.4] nonane-3, 8-diketone framework, has novel and feasible route, and provides a new route reference for synthesizing 2, 7-diazaspiro [4.4] nonane compounds.
B. The 2, 7-diazaspiro [4.4] nonane-3, 8-dione provided by the invention adopts sodium borohydride and iodine to reduce amide, excessive sodium borohydride is quenched by methanol, and residual iodine directly catalyzes (Boc) 2 O reaction to synthesize 2-Boc-2, 7-diazaspiro [4.4] nonane, so that the operation steps are reduced, and the yield is improved. Route references are provided for the synthesis of such compounds.
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
Although the present invention has been described in detail by way of preferred embodiments, the present invention is not limited thereto. Various equivalent modifications and substitutions may be made in the embodiments of the present invention by those skilled in the art without departing from the spirit and scope of the present invention, and it is intended that all such modifications and substitutions be within the scope of the present invention/be within the scope of the present invention as defined by the appended claims. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Example 1
12.4G (0.1 mol) of spiro [3.3] heptane-2, 6-dione, 15.3g (0.22 mol) of hydroxylamine hydrochloride and 26.2g (0.32 mol) of sodium acetate are mixed in 250mL of methanol under the protection of nitrogen, reacted for 3 hours under the reflux condition, cooled to room temperature, filtered, concentrated, and the crude product is beaten with 100mL of deionized water, filtered and dried to obtain spiro [3.3] heptane-2, 6-dione dioxime, 13.8g, yield 90% and GC98.7%. 1HNMR(400MHz,DMSO-d6 ) 8.62 (s, 1H), 3.10 (m, 4H).
Example 2
Spiro [3.3] heptane-2, 6-dione dioxime 15.4g (0.1 mol), 1-butyl-3-methylimidazole zinc chloride salt 0.62g (0.002 mol) and hexachlorocyclotriphosphazene 0.052g (0.15 mmol) were mixed in 80mL hexafluoroisopropanol under nitrogen protection, heated to 40-50 ℃ for 2 hours, cooled to room temperature, concentrated, and the crude product purified by column chromatography, eluting with ethyl acetate/n-hexane (v/v=1/1-2) to give 2, 7-diazaspiro [4.4] nonane-3, 8-dione, 12.6g, yield 82%, GC99%. 1HNMR(400MHz,DMSO-d6 ) 7.53 (s, 2H), 3.15 (s, 4H), 2.2 (s, 4H).
Comparative example 2
Under the protection of nitrogen, 15.4g (0.1 mol) of spiro [3.3] heptane-2, 6-dione dioxime, 0.62g (0.002 mol) of 1-butyl-3-methylimidazole aluminum chloride and 0.052g (0.15 mmol) of hexachlorocyclotriphosphazene are mixed in 80mL of hexafluoroisopropanol, the temperature is raised to 60-70 ℃ for reaction for 2 hours, the temperature is reduced to room temperature, the concentration is carried out, the crude product is purified by column chromatography, and the eluent ethyl acetate/n-hexane (v/v=1/1-2) is obtained to obtain 10.9g, yield 71%, GC98.5% of 2, 7-diazaspiro [4.4] nonane-3, 8-dione.
Example 3
15.4G (0.1 mol) of 2, 7-diazaspiro [4.4] nonane-3, 8-dione and 12.1g (0.32 mol) of sodium borohydride are mixed in 80ml of THF under nitrogen and cooled to 0-10 ℃. 56g (0.22 mol) of iodine is mixed with 200mL of THF and then slowly added into the reaction solution, the mixture is heated to reflux after the completion of the addition, the reaction is carried out for 5 hours, then the temperature is reduced to room temperature, 50mL of methanol is added, then (Boc) 2 O21.8g (0.1 mol) is added, the mixture is stirred for 1 hour at room temperature, 100mL of ammonia water (5%) is added after the completion of the reaction, the layers are separated, the aqueous layer is extracted twice with 50mL of diisopropyl ether, the organic layers are combined, the concentration is carried out, the crude product is purified by column chromatography, and the eluent ethyl acetate/n-hexane (v/v=1/6-10) is obtained, the 2-Boc-2, 7-diazaspiro [4.4] nonane, 15.4g is obtained, the yield is increased 68％,GC99％.1HNMR(400MHz,DMSO-d6)：3.48-3.28(m,4H),3.03(m,2H),2.88-2.78(m,2H),1.92(m,1H),1.87-1.73(m,4H),1.48(s,9H).
The foregoing is only a preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art, who is within the scope of the present invention, should be covered by the protection scope of the present invention by making equivalents and modifications to the technical solution and the inventive concept thereof.
Claims (8)
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