JPS5495553A - Production of 3,17-dihydroxypregn-5-ene-20-ine - Google Patents

Production of 3,17-dihydroxypregn-5-ene-20-ine

Info

Publication number
JPS5495553A
JPS5495553A JP140478A JP140478A JPS5495553A JP S5495553 A JPS5495553 A JP S5495553A JP 140478 A JP140478 A JP 140478A JP 140478 A JP140478 A JP 140478A JP S5495553 A JPS5495553 A JP S5495553A
Authority
JP
Japan
Prior art keywords
ene
ine
dione
hydroxypregn
androst
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.)
Granted
Application number
JP140478A
Other languages
Japanese (ja)
Other versions
JPS6135999B2 (en
Inventor
Susumu Sugano
Shinichiro Fujimori
Rikizo Furuya
Takezo Nakanome
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.)
Mitsubishi Kasei Corp
Original Assignee
Mitsubishi Kasei Corp
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 Mitsubishi Kasei Corp filed Critical Mitsubishi Kasei Corp
Priority to JP140478A priority Critical patent/JPS5495553A/en
Publication of JPS5495553A publication Critical patent/JPS5495553A/en
Publication of JPS6135999B2 publication Critical patent/JPS6135999B2/ja
Granted legal-status Critical Current

Links

Abstract

PURPOSE: Androst-4-ene-3,17-dione is ethynylated then the pH is adjusted to form 17-hydroxypregn-5-ene-20-ine-3-one, which is reduced to produce title compound useful for medicines in high yield.
CONSTITUTION: The selective ethynylation of the 17 carbonyl in androst-4-ene-3,17- dione is conducted in a hydrophilic organic solvent using a metal acetylide as alkali metal acetylide in an amount of 1 - 100, preferably 2 - 20 times the molar quantity of the dione, then the reaction mixture is adjusted in pH by adding a weak acid with pKa of less than 2 as acetic acid to 1 - 13 at a temperature of 50°C or lower to form 17-hydroxypregn-5-ene-20-ine-3-one. The product is separated and reduced with a reducing agent as metal hydride complex or borohydride compound at -30 - 70°C to obtain the objective compound.
COPYRIGHT: (C)1979,JPO&Japio
JP140478A 1978-01-10 1978-01-10 Production of 3,17-dihydroxypregn-5-ene-20-ine Granted JPS5495553A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP140478A JPS5495553A (en) 1978-01-10 1978-01-10 Production of 3,17-dihydroxypregn-5-ene-20-ine

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP140478A JPS5495553A (en) 1978-01-10 1978-01-10 Production of 3,17-dihydroxypregn-5-ene-20-ine

Publications (2)

Publication Number Publication Date
JPS5495553A true JPS5495553A (en) 1979-07-28
JPS6135999B2 JPS6135999B2 (en) 1986-08-15

Family

ID=11500546

Family Applications (1)

Application Number Title Priority Date Filing Date
JP140478A Granted JPS5495553A (en) 1978-01-10 1978-01-10 Production of 3,17-dihydroxypregn-5-ene-20-ine

Country Status (1)

Country Link
JP (1) JPS5495553A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54145647A (en) * 1978-05-09 1979-11-14 Mitsubishi Chem Ind Ltd Preparation of pregn-5-en-20-yne-3,17-diol

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5492949A (en) * 1977-12-28 1979-07-23 Mitsubishi Chem Ind Ltd Production of 3,17-dihydroxypregn-5-ene-29-ine

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5492949A (en) * 1977-12-28 1979-07-23 Mitsubishi Chem Ind Ltd Production of 3,17-dihydroxypregn-5-ene-29-ine

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54145647A (en) * 1978-05-09 1979-11-14 Mitsubishi Chem Ind Ltd Preparation of pregn-5-en-20-yne-3,17-diol

Also Published As

Publication number Publication date
JPS6135999B2 (en) 1986-08-15

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