Acetic Acid → 1alpha-Methyl-4-androstene-3beta,17beta,19-triol

HRID 371841Notes

Reaction equation

HRID 371841 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.[BH4-].[Na+].C(O)(=O)C>C(O)C>[CH3:22][C@@H:15]1[C@@:16]2([CH2:17][OH:18])[C:11]([CH2:10][CH2:9][C@@H:8]3[C@@H:19]2[CH2:20][CH2:21][C@@:3]2([CH3:4])[C@H:5]3[CH2:6][CH2:7][C@@H:2]2[OH:1])=[CH:12][C@@H:13]([OH:23])[CH2:14]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 2279742517beta,19-Dihydroxy-1alphamethyl-4-androsten-3-one

Product 1

HCID 705863741alpha-Methyl-4-androstene-3beta,17beta,19-triol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

17β,19-Dihydroxy-1α-methyl-4-androsten-3-one is dissolved in ethanol and sodium borohydride is added slowly under nitrogen. After stirring at room temperature for 4 hours, the solution is poured onto ice water containing a few drops of acetic acid. The solid which forms is filtered and recrystallized from ethanol to yield 1α-methyl-4-androstene-3β,17β,19-triol.

Workup

  1. filtrationThe solid which forms is filtered
  2. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3d99a8c8175645548a45cc069f250fe7
Source dataset
uspto-grants-1978_05
Patent number
US04087524

Reaction notes

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