Ammonium Chloride → Cholest-5-ene-1alpha,3beta-diol

HRID 2049945Notes

Reaction equation

HRID 2049945 reaction equation
[O:1]1[C@H:3]2[C:4](=[O:29])[CH:5]=[C:6]3[C@:26]([CH3:27])([C@@H:2]12)[C@@H:25]1[C@H:9]([C@H:10]2[C@:22]([CH3:28])([CH2:23][CH2:24]1)[C@@H:13]([C@H:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:12][CH2:11]2)[CH:8]=[CH:7]3.[Li].[Cl-].[NH4+]>N.O1CCCC1>[OH:1][C@@H:2]1[C@@:26]2([CH3:27])[C:6](=[CH:7][CH2:8][C@@H:9]3[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:28])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:21])[CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:5][C@@H:4]([OH:29])[CH2:3]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 139111081alpha,2alpha-Epoxycholesta-4,6-dien-3-one

Product 1

HCID 11112200Cholest-5-ene-1alpha,3beta-diol

Reagents, catalysts & solvents 1

HCID 21982362Ammonia tetrahydrofuranSolvent

Procedure

Barton et al, J.A.C.S. 95:8, 2748 (1973) describe reduction of 1α,2α-epoxycholesta-4,6-dien-3-one with large excesses of each of lithium metal and ammonium chloride in ammonia/tetrahydrofuran at reflux to obtain 1α,3β-dihydroxycholest-5-ene which is a precursor of 1α-hydroxyvitamin D3.

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-250f3c695fcb4d3a877fa31be8259cad
Source dataset
uspto-grants-1980_04
Patent number
US04199518

Reaction notes

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