3(R)-Pyrrolidinyloxyamine dihydrochloride → (3E,5S,6S,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-5,6,17-triol;hydrochloride

HRID 1182859Notes

Reaction equation

HRID 1182859 reaction equation
[OH:1][C@:2]12[C:19]([CH3:21])([CH3:20])[C:18](=O)[CH2:17][CH2:16][C@:15]1([CH3:23])[C@@H:14]1[C@H:5]([C@H:6]3[C@@:10]([CH2:12][CH2:13]1)([CH3:11])[C@@H:9]([OH:24])[CH2:8][CH2:7]3)[CH2:4][C@@H:3]2[OH:25].[ClH:26].Cl.[NH:28]1[CH2:32][CH2:31][C@@H:30]([O:33][NH2:34])[CH2:29]1>>[ClH:26].[NH:28]1[CH2:32][CH2:31][C@@H:30]([O:33]/[N:34]=[C:18]2/[C:19]([CH3:21])([CH3:20])[C@@:2]3([OH:1])[C@:15]([CH3:23])([CH2:16][CH2:17]/2)[C@@H:14]2[C@H:5]([C@H:6]4[C@@:10]([CH2:12][CH2:13]2)([CH3:11])[C@@H:9]([OH:24])[CH2:8][CH2:7]4)[CH2:4][C@@H:3]3[OH:25])[CH2:29]1

Participants

3

Reactant 2

HCID 667139183(R)-Pyrrolidinyloxyamine dihydrochlorideHCID 687322435alpha,6alpha,17beta-Trihydroxy-4,4-dimethylandrostan-3-one

Product 1

HCID 87553883(3E,5S,6S,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-5,6,17-triol;hydrochlorideYield 90%

Procedure

The title compound was prepared in 90% yield (121 mg) as described in Example 2 starting from 5α,6α,17β-trihydroxy-4,4-dimethylandrostan-3-one, (Preparation 5, 100 mg) and 3-(R)-pyrrolidinyloxyamine dihydrochloride (Preparation 12, 200 mg).

Sources & evidence

ORD record
ord-eacc3f39bcc14f6dbdbc1a1ac219f630
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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