3beta,17beta-Dihydroxyandrost-5-en-7-one → 3beta,17beta-Dihydroxyandrostane-7-one

HRID 910605Notes

Reaction equation

HRID 910605 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][C:6](=[O:22])[C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[OH:21])[CH2:3]1.C1COC23OCCOC2([C@]2(CC[C@H]4[C@@H](C(=O)CC5[C@]4(C)CCCC5)[C@@H]2C3)C)O1>>[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[CH:4]([CH2:5][C:6](=[O:22])[C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[OH:21])[CH2:3]1

Participants

3

Reactant 2

HCID 114266823beta,17beta-Dihydroxyandrost-5-en-7-oneHCID 6895071317,17-Bis(ethylendioxy)androstan-7-one

Product 1

HCID 669101493beta,17beta-Dihydroxyandrostane-7-oneYield 95.1%

Procedure

3β,17β-Dihydroxyandrostan-7-one was prepared in 96% yield from 3β,17β-dihydroxyandrost-5-en-7-one (700 mg) by the procedure described above for the preparation of 3,3:17,17-bis(ethylendioxy)androstane-7-one (Prepn. 9). The crude product was purified by flash chromatography (SiO2, hexane/acetone/CH2Cl2 10/10/10) to give 3β,17β-dihydroxyandrostane-7-one (670 mg). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.53 (bb, 1H), 4.44 (bb, 1H), 3.47-3.27 (m, 2H), 2.45-2.31 (m, 2H), 2.05-1.91 (m, 1H), 1.89-0.78 (m, 17H), 0.99 (s, 3H), 0.59 (s, 3H).

Workup

  1. customdescribed above for the preparation of 3,3
  2. customThe crude product was purified by flash chromatography (SiO2, hexane/acetone/CH2Cl2 10/10/10)

Sources & evidence

ORD record
ord-66a90e6c64f042a09f1773802c017e0d
Source dataset
uspto-grants-2011_09
Patent number
US08022203B2

Reaction notes

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