17beta,19-Dihydroxy-1alphamethyl-4-androsten-3-one → 17beta,19-Dihydroxy-1alpha-methyl-5-androsten-3-one

HRID 1390732Notes

Reaction equation

HRID 1390732 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:19]([CH2:20][CH2:21][C@:3]12[CH3:4])[C@:16]1([CH2:17][OH:18])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][C@@H:15]1[CH3:22])[CH2:10][CH2:9]3.CC(C)([O-])C.[K+]>CS(C)=O>[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:19]([CH2:20][CH2:21][C@:3]12[CH3:4])[C@:16]1([CH2:17][OH:18])[C:11]([CH2:12][C:13](=[O:23])[CH2:14][C@@H:15]1[CH3:22])=[CH:10][CH2:9]3

Participants

4

Reactant 2

HCID 2279742517beta,19-Dihydroxy-1alphamethyl-4-androsten-3-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 7060471217beta,19-Dihydroxy-1alpha-methyl-5-androsten-3-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 17β,19-dihydroxy-1α-methyl-4-androsten-3-one in dimethylsulfoxide is added to a solution of potassium t-butoxide in dimethylsulfoxide precooled to 20° C. The reaction mixture is stirred under nitrogen for 10 minutes at room temperature and then poured onto ice cold aqueous ammonium chloride solution with vigorous stirring. The precipitate is rapidly filtered under vacuum, washed well with water and air dried. Crystallization of this residue from an acetone-hexane solution furnishes pure 17β,19-dihydroxy-1α-methyl-5-androsten-3-one.

Workup

  1. customprecooled to 20° C
  2. additionpoured onto ice cold aqueous ammonium chloride solution with vigorous stirring
  3. filtrationThe precipitate is rapidly filtered under vacuum
  4. washwashed well with water and air
  5. customdried
  6. customCrystallization of this residue from an acetone-hexane solution

Sources & evidence

ORD record
ord-79d87f6484d3466f8b927b2e5d91208a
Source dataset
uspto-grants-1979_02
Patent number
US04139617

Reaction notes

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