Lithium → HCID 20739691, compound

HRID 1019016Notes

Reaction equation

HRID 1019016 reaction equation
[O:1]1[C@@:18]23[C@:19]4([CH3:28])[C:24](=[CH:25][CH2:26][C@@:2]12[C@H:3]1[C@:15]([CH3:29])([CH2:16][CH2:17]3)[C@@H:6]([C@H:7]([CH3:14])[CH2:8][CH2:9][CH2:10][CH:11]([CH3:13])[CH3:12])[CH2:5][CH2:4]1)[CH2:23][C@@H:22]([OH:27])[CH2:21][CH2:20]4.[Li]>C(NCC)C>[CH3:13][CH:11]([CH2:10][CH2:9][CH2:8][C@H:7]([C@@H:6]1[C@:15]2([CH3:29])[C@H:3]([C@H:2]3[C@:18]([OH:1])([CH2:17][CH2:16]2)[C@:19]2([CH3:28])[C:24]([CH2:23][C@@H:22]([OH:27])[CH2:21][CH2:20]2)=[CH:25][CH2:26]3)[CH2:4][CH2:5]1)[CH3:14])[CH3:12]

Participants

4

Reactant 2

HCID 3028194LithiumHCID 57263809HCID 57263809, compound

Product 1

HCID 20739691HCID 20739691, compoundYield 30.8%

Reagents, catalysts & solvents 1

HCID 8021DiethylamineSolvent

Procedure

8α,9α-Epoxycholest-5-en-3β-ol(200 mg) is dissolved in 13 ml diethylamine at −20° C. Lithium (100 mg) is added in small portions. The reaction mixture is stirred for 3 hours. After aqueous work-up, a crude product (207 mg) is isolated. Crystallization from diisopropylether yields cholest-5-ene-3β,9α-diol (62 mg).

Workup

  1. customAfter aqueous work-up, a crude product (207 mg) is isolated
  2. customCrystallization from diisopropylether

Sources & evidence

ORD record
ord-6fb0d75408044b0ca1f5708aed47d327
Source dataset
uspto-grants-2002_11
Patent number
US06486145B2

Reaction notes

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