GB865316A - Improvements in or relating to steroids and the manufacture thereof - Google Patents

Improvements in or relating to steroids and the manufacture thereof

Info

Publication number
GB865316A
GB865316A GB1480/58A GB148058A GB865316A GB 865316 A GB865316 A GB 865316A GB 1480/58 A GB1480/58 A GB 1480/58A GB 148058 A GB148058 A GB 148058A GB 865316 A GB865316 A GB 865316A
Authority
GB
United Kingdom
Prior art keywords
methyl
androstene
trihydroxy
androsten
dihydroxy
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
GB1480/58A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn Co
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 Upjohn Co filed Critical Upjohn Co
Publication of GB865316A publication Critical patent/GB865316A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises 3b , 11b , 17b -trihydroxy-17a -methyl-5-androstene, 3b , 11b , 17b -trihydroxy-17a -methyl-5-androstene-3b -acylates, 3b , 11b , 17b -trihydroxy-17a -methyl-5-androstene 11b ,17b -diacylates, 3b , 11b , 17b -trihydroxy-17a -methyl-5-andros-tene 3b , 11b , 17b -triacylates, 3b , 17b -dihydroxy- 17a -methyl- 5-androsten- 11-one, 3b , 17b -dihydroxy-17a -methyl-5-androsten-11-one 3b -acylate, and 3b , 17b -dihydroxy-17a -methyl-5-androsten-11-one 3b ,17b -diacylate, wherein the acyl radical is of a hydrocarbon carboxylic acid containing from 1-9 carbon atoms, inclusive, and a process for the production of 3b , 11b , 17b -trihydroxy-17a -methyl-5-androstene which comprises treating a 3, 11b , 17b -triacyloxy-17a -methyl-3, 5-androstadien wherein the acyl group is of an organic carboxylic acid preferably containing from 1-9 carbon atoms, inclusive, with an alkali metal borohydride to obtain the corresponding 3-hydroxy-11b , 17b -diacyloxy-17a -methyl-5-androstene and hydrolysing the thus obtained 11b ,17b -diacylate with lithium aluminium hydride to obtain 3b , 11b , 17b -trihydroxy-17a -methyl-5-androstene. Subsequently the 3b , 11b , 17b -trihydroxy-17a -methyl-5-androstene may be esterified to produce a 3-mono ester which is oxidised to the corresponding 3b -acyloxy-17b -hydroxy-17a -methyl-5-androsten-11-one. As alkali metal boro-hydrides there may be used sodium, potassium or lithium borohydride. As acylating agents there may be used the anhydrides, chlorides or bromides of organic carboxylic acids. Examples describe the preparation of 3b , 11b , 17b -trihydroxy-17a -methyl-5-androstene and the 11b ,17b -diacetate, -dipropionate, -dibutyrate, -dibenzoate, -divalerate, -dihexanoate, -diheptanoate, -dioctanoate, -diphenylacetate, -di (trimethyl-acetate) and -di(trifluoroacetate) thereof, the corresponding 3-monoesters thereof, the corresponding 3b , 11b , 17b -triesters and mixed esters thereof, 3b , 17b -dihydroxy-17a -methyl-5-androsten-11-one the 3b -acetate, benzoate &c., thereof and the corresponding 3b , 17b -diesters thereof. Specification 788,695 is referred to.
GB1480/58A 1957-02-14 1958-01-15 Improvements in or relating to steroids and the manufacture thereof Expired GB865316A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US865316XA 1957-02-14 1957-02-14

Publications (1)

Publication Number Publication Date
GB865316A true GB865316A (en) 1961-04-12

Family

ID=22199195

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1480/58A Expired GB865316A (en) 1957-02-14 1958-01-15 Improvements in or relating to steroids and the manufacture thereof

Country Status (1)

Country Link
GB (1) GB865316A (en)

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