HCID 86583589, compound → HCID 57062770, compound

HRID 1019013Notes

Reaction equation

HRID 1019013 reaction equation
[O:1]1[C@@:3]23[C@:23]([CH3:28])([CH2:24][CH2:25][C:26](=[O:27])[C@@H:2]12)[C:22]1[CH2:21][CH2:20][C@@:19]2([CH3:29])[C@@H:7]([CH2:8][CH2:9][C@@H:10]2[C@H:11]([CH3:18])[CH2:12][CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:6]=1[CH2:5][CH2:4]3>O1CCCC1>[CH3:17][CH:15]([CH2:14][CH2:13][CH2:12][C@H:11]([C@@H:10]1[C@:19]2([CH3:29])[C@H:7]([C:6]3[CH2:5][CH2:4][C@@:3]4([OH:1])[C@:23]([C:22]=3[CH2:21][CH2:20]2)([CH3:28])[CH2:24][CH2:25][C@H:26]([OH:27])[CH2:2]4)[CH2:8][CH2:9]1)[CH3:18])[CH3:16].[CH3:17][CH:15]([CH2:14][CH2:13][CH2:12][C@H:11]([C@@H:10]1[C@:19]2([CH3:29])[C@H:7]([C:6]3[CH2:5][CH2:4][C@@:3]4([OH:1])[C@:23]([C:22]=3[CH2:21][CH2:20]2)([CH3:28])[CH2:24][CH2:25][C@@H:26]([OH:27])[CH2:2]4)[CH2:8][CH2:9]1)[CH3:18])[CH3:16]

Participants

4

Reactant 1

HCID 86583589HCID 86583589, compound

Product 2

HCID 57062770HCID 57062770, compoundHCID 57149152HCID 57149152, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cholesta-5,8-diene-3-on is epoxidized in analogy to a literature procedure [J. Med. Chem. 39, 5092, (1996)] to give 4α,5-epoxy-5α-cholest-8-en-3-on. This is reduced as described below. 4α,5-Epoxy-5α-cholest-8-en-3-on (75 mg) is dissolved in 3 ml tetrahydrofuran. Lithiumaluminumhydride (30 mg) is added at room temperature. The reaction mixture is stirred for 15 hours. After aqueous work-up and column chromatography 5βcholest-8-ene-3β,5β-diol (19 mg) and 5βcholest-8-ene-3α,5β-diol (24 mg) are isolated.

Workup

  1. additionLithiumaluminumhydride (30 mg) is added at room temperature

Sources & evidence

ORD record
ord-08122fa38bbb4b909731ab2bc4e36fc2
Source dataset
uspto-grants-2002_11
Patent number
US06486145B2

Reaction notes

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