GB725763A - Optically active 3-hydroxy-n-methyl-morphinanes and process for the manufacture thereof - Google Patents
Optically active 3-hydroxy-n-methyl-morphinanes and process for the manufacture thereofInfo
- Publication number
- GB725763A GB725763A GB17767/53A GB1776753A GB725763A GB 725763 A GB725763 A GB 725763A GB 17767/53 A GB17767/53 A GB 17767/53A GB 1776753 A GB1776753 A GB 1776753A GB 725763 A GB725763 A GB 725763A
- Authority
- GB
- United Kingdom
- Prior art keywords
- morphinane
- tartrate
- hydroxy
- methyl
- optically active
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B57/00—Separation of optically-active compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The optical isomers of 3-hydroxy-N-methylmorphinane are prepared by resolving 1-(p-methoxybenzyl)-2-methyl-1 : 2 : 3 : 4 : 5 : 6 : 7 : 8-octahydroisoquinoline by means of an optically active acid and cyclising the optical antipodes separately. The latter may be isolated as tartrates which are subsequently converted into the free bases. Resolution of the isoquinoline may be effected by fractional crystallization of the tartrate from water or methanol or a mixture of the two. The tartrate which crystallizes first is laevorotatory in ether and (after conversion to the free base) gives the d-(+)-morphinane on cyclizing with phosphoric acid. From the mother liquor is obtained the tartrate which is dextrorotatory in ether and this can be converted into free base and cyclised to the l-(-)-morphinane. Alternatively the crude mother liquor can be cyclised directly and resolution completed at the morphinane stage. The process is exemplified.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH725763X | 1952-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB725763A true GB725763A (en) | 1955-03-09 |
Family
ID=4531910
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17767/53A Expired GB725763A (en) | 1952-06-30 | 1953-06-26 | Optically active 3-hydroxy-n-methyl-morphinanes and process for the manufacture thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB725763A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102241630A (en) * | 2011-05-20 | 2011-11-16 | 杭州保灵集团有限公司 | Preparation method of dimethylmorphinan phosphate used as cough medicine |
-
1953
- 1953-06-26 GB GB17767/53A patent/GB725763A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102241630A (en) * | 2011-05-20 | 2011-11-16 | 杭州保灵集团有限公司 | Preparation method of dimethylmorphinan phosphate used as cough medicine |
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