3(R)-Pyrrolidinyloxyamine dihydrochloride → (3E,4R,6S,8R,9S,10R,13S,14S)-4-ethyl-6-hydroxy-10,13-dimethyl-3-[(3R)-pyrrolidin-3-yl]oxyimino-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-one;hydrochloride

HRID 1182868Notes

Reaction equation

HRID 1182868 reaction equation
[CH2:1]([C@H:3]1[C:20](=O)[CH2:19][CH2:18][C@@:17]2([CH3:22])[CH:4]1[C@@H:5]([OH:24])[CH2:6][C@@H:7]1[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]1[CH2:9][CH2:10][C:11]2=[O:23])[CH3:2].[ClH:25].Cl.[NH:27]1[CH2:31][CH2:30][C@@H:29]([O:32][NH2:33])[CH2:28]1>>[ClH:25].[NH:27]1[CH2:31][CH2:30][C@@H:29]([O:32]/[N:33]=[C:20]2/[C@H:3]([CH2:1][CH3:2])[CH:4]3[C@:17]([CH3:22])([CH2:18][CH2:19]/2)[C@@H:16]2[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]2)([CH3:13])[C:11](=[O:23])[CH2:10][CH2:9]4)[CH2:6][C@@H:5]3[OH:24])[CH2:28]1

Participants

3

Reactant 2

HCID 667139183(R)-Pyrrolidinyloxyamine dihydrochlorideHCID 687318194beta-Ethyl-6alpha-hydroxyandrostan-3,17-dione

Product 1

HCID 87571573(3E,4R,6S,8R,9S,10R,13S,14S)-4-ethyl-6-hydroxy-10,13-dimethyl-3-[(3R)-pyrrolidin-3-yl]oxyimino-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-one;hydrochloride

Procedure

The title compound was obtained in 90% yield following the procedure described in Example 30 starting from 4β-ethyl-6α-hydroxyandrostan-3,17-dione (Preparation 27, 137 mg) and 3-(R)-pyrrolidinyloxyamine dihydrochloride (Preparation 12, 160 mg). The crude product was triturated with Et2O and the resulting precipitate was filtered to give the title compound I-bx.

Workup

  1. customThe crude product was triturated with Et2O
  2. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-22825a639d064a5eb6fd0006760d7dec
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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