Water → Epiandrosterone

HRID 467451

Reaction equation

HRID 467451 reaction equation
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:24])[CH2:6]1)(=O)C.[OH-].[Na+].O>CO>[OH:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:24])[CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 9087403beta-Acetoxy-5alpha-androstan-17-one

Product 1

HCID 441302EpiandrosteroneYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5 (1 g, 3.00 mmol), NaOH 0.12 g (3.44 mmol) in methanol was refluxed for 10 min, cooled to room temperature and treated with water. The resulting precipitate was filtered off and washed with water to afford crude product 6 (0.82 g, 95%).

Workup

  1. temperaturewas refluxed for 10 min
  2. filtrationThe resulting precipitate was filtered off
  3. washwashed with water

Sources & evidence

ORD record
ord-ae5f46f7bef043fb87e21b3a77341060
Source dataset
uspto-grants-2014_01
Patent number
US08623849B2

Linked notes

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