GB933958A - 16ªá-alkyl-pregnane compounds and process for their manufacture - Google Patents

16ªá-alkyl-pregnane compounds and process for their manufacture

Info

Publication number
GB933958A
GB933958A GB3456859A GB3456859A GB933958A GB 933958 A GB933958 A GB 933958A GB 3456859 A GB3456859 A GB 3456859A GB 3456859 A GB3456859 A GB 3456859A GB 933958 A GB933958 A GB 933958A
Authority
GB
United Kingdom
Prior art keywords
methyl
keto
hydroxy
alkyl
pregnene
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
GB3456859A
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.)
BASF Schweiz AG
Original Assignee
Ciba AG
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
Priority claimed from CH6488858A external-priority patent/CH368490A/en
Priority claimed from CH6669558A external-priority patent/CH372302A/en
Application filed by Ciba AG filed Critical Ciba AG
Publication of GB933958A publication Critical patent/GB933958A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • 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
    • 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) a process for preparing 16a -alkyl-pregnanes by reacting a D 16-20-keto-pregnene with an alkyl magnesium halide in presence of a cuprous halide and tetrahydrofuran and absence of an alkyl halide and decomposing the resulting metalenolate either with a hydrolysing agent to form a 16a -alkyl-20-keto-pregnane or with an acylating agent to form a 20-enol-ester thereof; and (2) the 20-enol-acylates of D 5-3b -acyloxy- 16a -methyl- 20-keto pregnenes, 3b :11a -diacyloxy- 16a -methyl- 20-keto-allopregnanes, 3b -acyloxy-16a -methyl-11:20-diketo-allopregnanes and D 4-3:20-diketo-16a -methyl-pregnenes; and D 5:17(20) -3b :20-diacetoxy- 11-keto- 16a -methyl-pregnadiene and D 5:17(20)- 3b :11a :20-triacetoxy- 16a -methylpregnadiene. Suitable hydrolysing agents are dilute acids or ammonium chloride and suitable acylating agents are the anhydrides, halides or quaternary amides of aliphatic, araliphatic, aromatic or heterocyclic carboxylic acids such as lower fatty acids, phenylacetic acid, p-nitrophenylacetic acid, benzoic acid and substituted benzoic acids and furane-2-carboxylic acid. Examples describe the preparation of compounds representative of the classes described above and of D 17(20)-3a :20- diacetoxy-11-keto- 16a -methyl-pregnene by the acylating process and of 3a -and 3b -hydroxy- 11:20-diketo- 16a -methylallopregnanes, 3b :11a -dihydroxy-16a -methyl-20-ketoallopregnane, D 5-3b -hydroxy- 16a -methyl-20-keto-pregnene and the corresponding 21-hydroxy compound, 3b -hydroxy-16a -methyl-20-keto-pregnane and 16a -methyl-progesterone by the hydrolysing process, all except the last-named of these 20-ketones being subsequently converted to acetates thereof by reaction with acetic anhydride in pyridine. Similarly, D 4-3,20-dioxo-21-acetoxy-16a -methyl-pregnene is prepared from D 5,16-3-ethylenedioxy- 21-acetoxy- 20-oxo-pregnadiene. A list of further starting materials containing, in addition to the features disclosed above, D 9(11), D 1:4 and D 3:5 double bonds, free or ketalized oxo groups in the 6-, 7- or 12-positions, and a 3-ethoxy group, is also provided, and reference is also made to the conversion of 3- and 21-ols into esters and ethers thereof. The conversion of 16a -methyl-progesterone-20-enol acetate to 16a -methyl-17a-hydroxy-progesterone is also described.
GB3456859A 1958-10-10 1959-10-12 16ªá-alkyl-pregnane compounds and process for their manufacture Expired GB933958A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
CH6488858A CH368490A (en) 1958-10-10 1958-10-10 Process for the preparation of 16a-alkyl-20-keto-steroids
CH6669558A CH372302A (en) 1958-11-28 1958-11-28 Process for the preparation of 17 (20) -16a-alkyl-20-acyloxy-steroids of the 5a and 5ss-pregnane series
CH7829259 1959-09-16

Publications (1)

Publication Number Publication Date
GB933958A true GB933958A (en) 1963-08-14

Family

ID=27178512

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3456859A Expired GB933958A (en) 1958-10-10 1959-10-12 16ªá-alkyl-pregnane compounds and process for their manufacture

Country Status (1)

Country Link
GB (1) GB933958A (en)

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