17beta-Methoxycarbonyl-5alpha-androst-2-en-11-one → 5alpha-Androst-2-en-11-one 17beta-carboxylic acid

HRID 267632Notes

Reaction equation

HRID 267632 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([C:22](=[O:24])[CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C@H:14]([CH2:15][CH:16]=[CH:17][CH2:18]1)[CH2:13][CH2:12]3)=[O:4]>[OH-].[K+]>[CH3:7][C@:6]12[CH2:23][C:22](=[O:24])[C@H:21]3[C@@H:11]([CH2:12][CH2:13][C@@H:14]4[C@:19]3([CH3:20])[CH2:18][CH:17]=[CH:16][CH2:15]4)[C@@H:8]1[CH2:9][CH2:10][C@@H:5]2[C:3]([OH:4])=[O:2]

Participants

3

Reactant 1

HCID 2278825117beta-Methoxycarbonyl-5alpha-androst-2-en-11-one

Product 1

HCID 227882705alpha-Androst-2-en-11-one 17beta-carboxylic acidYield 57.4%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

A solution of 17β-methoxycarbonyl-5α-androst-2-en-11-one (4.6g.,) in 3% ethanolic potassium hydroxide (50 ml.) was refluxed under N2 for 36 hr. and then concentrated to small volume prior to pouring into water. After acidification the solid product was filtered, dried and recrystallised from chloroform/benzene to give the title compound (2.53 g.), m.p. 201°-214°; [α]D + 129°

Workup

  1. concentrationand then concentrated to small volume
  2. additionto pouring into water
  3. filtrationAfter acidification the solid product was filtered
  4. customdried
  5. customrecrystallised from chloroform/benzene

Sources & evidence

ORD record
ord-dc1aa3997f8a48b384c588eab523b785
Source dataset
uspto-grants-1976_03
Patent number
US03943124

Reaction notes

Loading…