3alpha-Acetylthio-6-methyleneandrostan-17-one → 3alpha-Mercapto-6-methyleneandrostan-17-one

HRID 42132Notes

Reaction equation

HRID 42132 reaction equation
C([S:4][C@@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[CH:7]([C:8](=[CH2:25])[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>CO.[OH-].[Na+]>[SH:4][C@@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[CH:7]([C:8](=[CH2:25])[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

4

Reactant 1

HCID 866355983alpha-Acetylthio-6-methyleneandrostan-17-one

Product 1

HCID 866355993alpha-Mercapto-6-methyleneandrostan-17-oneYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3α-acetylthio-6-methyleneandrostan-17-one (210 mg) in MeOH (3 mL), 1N NaOH (0.6 mL) was added. After 1 h at room temperature 5% NaH2PO4 aqueous solution was added and the mixture extracted with Et2O (2×20 mL). The combined organic extracts were washed with brine, dried over Na2SO4 and evaporated to dryness to give the title compound (185 mg, 100%).

Workup

  1. extractionthe mixture extracted with Et2O (2×20 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-e36a9c4bb47b4c7fa832ce815272e8eb
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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