Aluminium lithium hydride → 4,4-Dimethyl-24-dimethylamino-5alpha-chola-8,14-dien-3beta-ol

HRID 479309Notes

Reaction equation

HRID 479309 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH3:37])[C:9](=O)[CH2:10][CH2:11][C@H:12]([C@@H:14]1[C@:31]2([CH3:32])[C:17]([C:18]3[CH2:19][CH2:20][C@@H:21]4[C@:26]([C:28]=3[CH2:29][CH2:30]2)([CH3:27])[CH2:25][CH2:24][C@H:23]([OH:33])[C:22]4([CH3:35])[CH3:34])=[CH:16][CH2:15]1)[CH3:13]>C1COCC1>[CH3:35][C:22]1([CH3:34])[C@@H:23]([OH:33])[CH2:24][CH2:25][C@@:26]2([CH3:27])[C@H:21]1[CH2:20][CH2:19][C:18]1[C:17]3[C@:31]([CH3:32])([CH2:30][CH2:29][C:28]=12)[C@@H:14]([C@H:12]([CH3:13])[CH2:11][CH2:10][CH2:9][N:8]([CH3:37])[CH3:7])[CH2:15][CH:16]=3

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 698734753beta-hydroxy-4,4-dimethyl-5alpha-chola-8,14-dien-24-oic acid-N,N-dimethyl amide

Product 1

HCID 698734774,4-Dimethyl-24-dimethylamino-5alpha-chola-8,14-dien-3beta-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound is synthesised by lithium aluminium hydride reduction in THF of 3β-hydroxy-4,4-dimethyl-5α-chola-8,14-dien-24-oic acid-N,N-dimethyl amide. 1H-NMR (CDCl3, 400 MHz): δ=5.35 (1H, s); 3.23 (1H, m); 2.85 (2H, m); 2.72 (6H, s).

Sources & evidence

ORD record
ord-85d22364071c48a2980ba52db680eeeb
Source dataset
uspto-grants-2003_11
Patent number
US06645953B2

Reaction notes

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