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GB852683A - 6-methyl steroid compounds and process for the preparation thereof - Google Patents

6-methyl steroid compounds and process for the preparation thereof

Info

Publication number
GB852683A
GB852683A GB3087857A GB3087857A GB852683A GB 852683 A GB852683 A GB 852683A GB 3087857 A GB3087857 A GB 3087857A GB 3087857 A GB3087857 A GB 3087857A GB 852683 A GB852683 A GB 852683A
Authority
GB
United Kingdom
Prior art keywords
acyloxy
methyl
give
pregn
effected
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
Application number
GB3087857A
Inventor
Vladimir Petrow
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BDH Chemicals Ltd
Original Assignee
BDH Chemicals Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BDH Chemicals Ltd filed Critical BDH Chemicals Ltd
Priority to GB3087857A priority Critical patent/GB852683A/en
Priority to CH6451958A priority patent/CH376500A/en
Publication of GB852683A publication Critical patent/GB852683A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J75/00—Processes for the preparation of steroids in general

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)

Abstract

The invention comprises (1) steroids of the general formula: <FORM:0852683/IV(b)/1> (wherein R is hydrogen or an acyl group of at most 10 carbon atoms) ; (2) 3b :17a -dihydroxy-6-methyl-pregn-5-en-20-one and the 17-acetyl, 17-propionyl, 17-hexanoyl, 17-decanoyl, 3-acetyl and 3:17-diacetyl derivatives thereof; and (3) a process for the preparation of steroids of the above general formula by oxidising 3b -hydroxy-or a 3b -acyloxy-6-methyl-pregna-5:16-dien-20-one to the 16a :17a -epoxide, acylating this if desired and then treating it with a hydrogen halide to give the 16b -halogeno-17a -hydroxyderivative and reductively dehalogenating this to give 3b :17a -dihydroxy- or a 3b -acyloxy-17a -hydroxy-6-methyl-pregn-5-en-20-one, acylating this to give a 3b -acyloxy-17a -acyloxy-6-methylpregn-5-en-20-one, preferentially hydrolysing this at the 3-position and oxidising the 3-ol to give a 17a -acyloxy-6a -methyl-pregn-4-ene-3:20-dione which may subsequently be saponified to the 17a -ol. The first oxidation (during which partial or complete saponification of the 3b -acyloxy group may occur) may be effected with hydrogen peroxide in alkaline alcoholic solution, the epoxide so formed treated with hydrogen halide in a solvent at 25 DEG C. or below, the dehalogenation effected with Raney nickel in ethanol at room temperature, the acylation of the 17a -hydroxyl group performed by treatment with an acid anhydride and toluene p-sulphonic acid catalyst, the preferential hydrolysis carried out with hot ethanolic or methanolic hydrochloric acid, the second oxidation effected by the Oppenauer method and the final saponification brought about with alcoholic alkali. Examples are given. Specifications 851,742 and 852,684 are referred to.
GB3087857A 1957-10-02 1957-10-02 6-methyl steroid compounds and process for the preparation thereof Expired GB852683A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB3087857A GB852683A (en) 1957-10-02 1957-10-02 6-methyl steroid compounds and process for the preparation thereof
CH6451958A CH376500A (en) 1957-10-02 1958-09-30 Process for the preparation of 17a-acyloxy-6a-methylpregn-4-ene-3,20-dione

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3087857A GB852683A (en) 1957-10-02 1957-10-02 6-methyl steroid compounds and process for the preparation thereof

Publications (1)

Publication Number Publication Date
GB852683A true GB852683A (en) 1960-10-26

Family

ID=10314532

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3087857A Expired GB852683A (en) 1957-10-02 1957-10-02 6-methyl steroid compounds and process for the preparation thereof

Country Status (2)

Country Link
CH (1) CH376500A (en)
GB (1) GB852683A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4440684A (en) * 1982-02-05 1984-04-03 Schering Aktiengesellschaft Process for the preparation of 6-methyl-Δ4,6 -3-keto steroids

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5309823A (en) * 1992-04-15 1994-05-10 Allen Dillis V Coffee brewing assembly

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4440684A (en) * 1982-02-05 1984-04-03 Schering Aktiengesellschaft Process for the preparation of 6-methyl-Δ4,6 -3-keto steroids

Also Published As

Publication number Publication date
CH376500A (en) 1964-04-15

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