3beta-Acetoxyandrostane-7,17-dione → 3beta-Hydroxyandrostane-7,17-dione

HRID 42108

Reaction equation

HRID 42108 reaction equation
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[CH:7]([CH2:8][C:9](=[O:25])[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>CO.[OH-].[Na+]>[OH:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[CH:7]([CH2:8][C:9](=[O:25])[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

4

Reactant 1

HCID 690113133beta-Acetoxyandrostane-7,17-dione

Product 1

HCID 690080933beta-Hydroxyandrostane-7,17-dioneYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3β-acetoxyandrostane-7,17-dione in MeOH (156 mL), 5N NaOH (54 mL) was added. After stirring at room temperature for 10 min the solution was evaporated and the residue extracted with CH2Cl2 (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give 3β-hydroxyandrostane-7,17-dione (1.70 g, 95%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 4.56 (1H, d), 3.35 (1H, m), 2.66-0.87 (20H, m), 1.02 (3H, s), 0.76 (3H, s).

Workup

  1. customwas evaporated
  2. extractionthe residue extracted with CH2Cl2 (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-61c03a0824cc445b93973dcacbb44717
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Linked notes

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