Hydroxyamine hydrochloride → HCID 86736926, compound

HRID 2049475Notes

Reaction equation

HRID 2049475 reaction equation
[CH2:1]([O:3][C@H:4]1[CH2:21][C@@:20]2([CH3:22])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[C:18](=O)[CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[CH2:24])[CH2:6][C@@H:5]1[OH:25])[CH3:2].Cl.[NH2:27][OH:28]>C(O)C.[OH-].[Na+]>[CH2:1]([O:3][C@H:4]1[CH2:21][C@@:20]2([CH3:22])[C@@H:7]([CH2:8][CH2:9][C@@H:10]3[C@@H:19]2[C:18](=[N:27][OH:28])[CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[CH2:24])[CH2:6][C@@H:5]1[OH:25])[CH3:2]

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 12796461HCID 12796461, compound

Product 1

HCID 86736926HCID 86736926, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2β-ethoxy-3α-hydroxy-17-methylene-5α-androstan-11-one (1.75 g) in ethanol (50 ml) was added to a mixture of hydroxylamine hydrochloride (3.6 g) in 50% sodium hydroxide solution (14 ml) and the resulting suspension was stirred and refluxed for 35 hours. Most of the solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate and water. Evaporation of the washed organic layer and crystallization of the residue from ethyl acetate afford the title compound (1.4 g), m.p. 97°-99°, [α]D +44.1°.

Workup

  1. temperaturerefluxed for 35 hours
  2. customMost of the solvent was evaporated in vacuo
  3. customthe residue was partitioned between ethyl acetate and water
  4. customEvaporation of the washed organic layer and crystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-40d06a4a5cd942f5a82da96e5d5eb64e
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

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