Ammonia → HCID 54243345, compound

HRID 440728Notes

Reaction equation

HRID 440728 reaction equation
C([S:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C: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])=[CH:6]1)(=O)C.N>CO>[SH:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C: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])=[CH:6]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 54031575HCID 54031575, compound

Product 1

HCID 54243345HCID 54243345, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.3 g of 3β-acetylthio-androst-4-en-17-one (IV-a, Prep 7) in 20 ml of methanol, was saturated with gaseous ammonia and kept on standing for 3 hrs at room temperature. The mixture was evaporated to dryness under reduced pressure and purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 95/5 as eluant to give 1.1 g of the title compound (IIIa) as a white solid.

Workup

  1. customThe mixture was evaporated to dryness under reduced pressure
  2. custompurified by flash-chromatography (SiO2)

Sources & evidence

ORD record
ord-86feae38c0044ef9a1293a0b995c547c
Source dataset
uspto-grants-1996_05
Patent number
US05521167

Reaction notes

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