3(R)-Pyrrolidinyloxyamine dihydrochloride → HCID 86635556, compound

HRID 42075Notes

Reaction equation

HRID 42075 reaction equation
[CH3:1][C@@H:2]1[CH:19]2[C@:14]([CH3:21])([CH2:15][CH2:16][C:17](=O)[CH2:18]2)[C@@H:13]2[C@H:4]([C@H:5]3[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]3)[CH2:3]1.[ClH:23].Cl.[NH:25]1[CH2:29][CH2:28][C@@H:27]([O:30][NH2:31])[CH2:26]1>O>[ClH:23].[NH:25]1[CH2:29][CH2:28][C@@H:27]([O:30][N:31]=[C:17]2[CH2:16][CH2:15][C@@:14]3([CH3:21])[CH:19]([C@@H:2]([CH3:1])[CH2:3][C@@H:4]4[C@@H:13]3[CH2:12][CH2:11][C@@:9]3([CH3:10])[C@H:5]4[CH2:6][CH2:7][C:8]3=[O:22])[CH2:18]2)[CH2:26]1

Participants

4

Reactant 2

HCID 667139183(R)-Pyrrolidinyloxyamine dihydrochlorideHCID 690079826alpha-Methylandrostane-3,17-dione

Product 1

HCID 86635556HCID 86635556, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Prepared in 70% yield as described in Example 1 starting from 6α-methylandrostane-3,17-dione (II-ai, Prepn. 19) and 3-(R)-pyrrolidinyloxyamine dihydrochloride (III-e, Prepn. 5). The crude product was dissolved in H2O and freeze-dried to give the title compound I-ax. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 9.03 (2H, bb), 4.73 (1H, m), 3.30-3.02 (5H, m), 2.45-0.56 (22H, m), 0.87 (3H, m), 0.84 (3H, s), 0.78 (3H, s).

Workup

  1. customPrepared in 70% yield
  2. customfreeze-dried

Sources & evidence

ORD record
ord-dde115fecb644e73af38d9a0dea562a7
Source dataset
uspto-grants-2013_09
Patent number
US08536160B2

Reaction notes

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