Aluminium lithium hydride → HCID 69411676, compound

HRID 2187282Notes

Reaction equation

HRID 2187282 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C@H:6]([C@@H:8]1[C@:25]2([CH3:26])[C:11]([C:12]3[CH2:13][CH2:14][C@@H:15]4[C@:20]([C:22]=3[CH2:23][CH2:24]2)([CH3:21])[CH2:19][CH2:18][C@H:17]([O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[C:16]4([CH3:36])[CH3:35])=[CH:10][CH2:9]1)[CH3:7].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Si:28]([O:27][C@H:17]1[CH2:18][CH2:19][C@@:20]2([CH3:21])[C@@H:15]([CH2:14][CH2:13][C:12]3[C:11]4[C@:25]([CH3:26])([CH2:24][CH2:23][C:22]=32)[C@@H:8]([C@H:6]([CH3:7])[CH2:5][CH2:4][CH2:3][OH:2])[CH2:9][CH:10]=4)[C:16]1([CH3:35])[CH3:36])([C:31]([CH3:34])([CH3:32])[CH3:33])([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69410951HCID 69410951, compound

Product 1

HCID 69411676HCID 69411676, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3β-tert-Butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24-oic acid methyl ester (5.29 g) is reduced with lithium aluminium hydride (1.75 g) in 300 ml of THF at room temperature. After aqueous work-up and crystallisation from ethanol/water, 4.58 g of 3β-tert-butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24-ol is isolated.

Workup

  1. customAfter aqueous work-up and crystallisation from ethanol/water

Sources & evidence

ORD record
ord-b12ac8a548224043a47322a08ebe7bfb
Source dataset
uspto-grants-2002_06
Patent number
US06407086B2

Reaction notes

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