3(R)-Pyrrolidinyloxyamine dihydrochloride → (1S,2R,5E,7S,9S,11S,12S,15S,16S)-2,6,6,16-tetramethyl-5-[(3R)-pyrrolidin-3-yl]oxyimino-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-15-ol;hydrochloride

HRID 1182862Notes

Reaction equation

HRID 1182862 reaction equation
[O:1]1[C@H:3]2[CH2:4][C@@H:5]3[C@@H:14]([C@@:15]4([CH3:23])[CH2:16][CH2:17][C:18](=O)[C:19]([CH3:21])([CH3:20])[C@:2]124)[CH2:13][CH2:12][C@@:10]1([CH3:11])[C@H:6]3[CH2:7][CH2:8][C@@H:9]1[OH:24].[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:18]2/[C:19]([CH3:21])([CH3:20])[C@:2]34[O:1][C@H:3]3[CH2:4][C@@H:5]3[C@@H:14]([C@@:15]4([CH3:23])[CH2:16][CH2:17]/2)[CH2:13][CH2:12][C@@:10]2([CH3:11])[C@H:6]3[CH2:7][CH2:8][C@@H:9]2[OH:24])[CH2:28]1

Participants

3

Reactant 2

HCID 667139183(R)-Pyrrolidinyloxyamine dihydrochlorideHCID 866491775alpha,6alpha-Epoxy-17beta-hydroxy-4,4-dimethylandrostan-3-one

Product 1

HCID 87572667(1S,2R,5E,7S,9S,11S,12S,15S,16S)-2,6,6,16-tetramethyl-5-[(3R)-pyrrolidin-3-yl]oxyimino-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadecan-15-ol;hydrochlorideYield 75%

Procedure

Prepared in 75% yield (51 mg) as described in Example 2 starting from 5α,6α-epoxy-17β-hydroxy-4,4-dimethylandrostan-3-one, (Preparation 8, 50 mg) and 3-(R)-pyrrolidinyloxyamine dihydrochloride (Preparation 12, 105 mg).

Workup

  1. customPrepared in 75% yield (51 mg)

Sources & evidence

ORD record
ord-6441a0eda6274083a4174e29638a54cd
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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