3(R)-Pyrrolidinyloxyamine dihydrochloride → (3E,5S,8S,9S,10R,13S,14S,17S)-4,4,10,13-tetramethyl-3-[(3R)-pyrrolidin-3-yl]oxyimino-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-5,17-diol;hydrochloride

HRID 1182869Notes

Reaction equation

HRID 1182869 reaction equation
[CH3:1][C:2]1([CH3:24])[C:19](=O)[CH2:18][CH2:17][C@@:16]2([CH3:21])[C@@:3]1([OH:23])[CH2:4][CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[OH:22].[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:19]2/[C:2]([CH3:1])([CH3:24])[C@@:3]3([OH:23])[C@:16]([CH3:21])([CH2:17][CH2:18]/2)[C@@H:15]2[C@H:6]([C@H:7]4[C@@:11]([CH2:13][CH2:14]2)([CH3:12])[C@@H:10]([OH:22])[CH2:9][CH2:8]4)[CH2:5][CH2:4]3)[CH2:28]1

Participants

3

Reactant 2

HCID 667139183(R)-Pyrrolidinyloxyamine dihydrochlorideHCID 687291764,4-Dimethyl-5alpha,17beta-dihydroxyandrostan-3-one

Product 1

HCID 87573863(3E,5S,8S,9S,10R,13S,14S,17S)-4,4,10,13-tetramethyl-3-[(3R)-pyrrolidin-3-yl]oxyimino-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-5,17-diol;hydrochloride

Procedure

The title compound was obtained in 51% yield following the procedure described in Example 2 and starting from 4,4-dimethyl-5α,17β-dihydroxyandrostan-3-one (Preparation 28, 33 mg) and 3-(R)-pyrrolidinyloxyamine dihydrochloride (Preparation 12, 69 mg). The crude product was triturated with Et2O and the resulting precipitate was filtered to give the title compound I-by.

Workup

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

Sources & evidence

ORD record
ord-4617611e812f4a1aafdfd6b557fc366f
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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