1alpha,2alpha-Epoxy-25-hydroxycholesta-4,6-dien-3-one → 1alpha,25-Dihydroxycholesta-4,6-dien-3-one

HRID 651949Notes

Reaction equation

HRID 651949 reaction equation
[O:1]1[C@H:3]2[C:4](=[O:30])[CH:5]=[C:6]3[C@:27]([CH3:28])([C@@H:2]12)[C@@H:26]1[C@H:9]([C@H:10]2[C@:23]([CH3:29])([CH2:24][CH2:25]1)[C@@H:13]([C@H:14]([CH3:22])[CH2:15][CH2:16][CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])[CH2:12][CH2:11]2)[CH:8]=[CH:7]3>[Zn].C(O)(=O)C>[OH:1][C@@H:2]1[C@@:27]2([CH3:28])[C:6]([CH:7]=[CH:8][C@@H:9]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:29])[C@H:10]3[CH2:11][CH2:12][C@@H:13]2[C@H:14]([CH3:22])[CH2:15][CH2:16][CH2:17][C:18]([OH:21])([CH3:20])[CH3:19])=[CH:5][C:4](=[O:30])[CH2:3]1

Participants

4

Reactant 1

HCID 139111261alpha,2alpha-Epoxy-25-hydroxycholesta-4,6-dien-3-one

Product 1

HCID 545451311alpha,25-Dihydroxycholesta-4,6-dien-3-one

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

The epoxide from (b) was treated with zinc dust and acetic acid as described in Example 2 (a) to yield 1α,25-dihydroxycholesta-4,6-dien-3-one, which was then converted to the trimethylsilyl ether and reduced with lithium/liquid ammonia as described in Example 2 (b). The title compound obtained in this way, (m.p. 171-173 solidifies and remelts at 178°-179°; [α]D -35° in CHCl2) exhibited n.m.r. peaks at δ0.68, 1.02 (methyl groups), δ1.18 (gem-dimethyl groups), δ3.83 (1 proton, narrow signal, 1β-H), δ3.6-4.3 (1 proton, broad signal, 3α-H) and δ5.57 (1-proton, multiplet, 6-H). The 3-monobenzoate thereof melts at 212°-216°; [α]D -20° in CHCl3).

Sources & evidence

ORD record
ord-d0469c3600c243e0bb4d2ef51e7635a3
Source dataset
uspto-grants-1987_06
Patent number
US04670190

Reaction notes

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