Ethanol hydrochloride → 4,4-Dimethyl-24-phenylamino-5alpha-chola-8,14-dien-3beta-ol

HRID 2187273Notes

Reaction equation

HRID 2187273 reaction equation
[Si]([O:8][C@H:9]1[CH2:37][CH2:36][C@@:35]2([CH3:38])[C@@H:11]([CH2:12][CH2:13][C:14]3[C:15]4[C@:31]([CH3:39])([CH2:32][CH2:33][C:34]=32)[C@@H:18]([C@H:19]([CH3:30])[CH2:20][CH2:21][CH2:22][NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:17][CH:16]=4)[C:10]1([CH3:41])[CH3:40])(C(C)(C)C)(C)C.C(O)C.Cl>>[CH3:41][C:10]1([CH3:40])[C@@H:9]([OH:8])[CH2:37][CH2:36][C@@:35]2([CH3:38])[C@H:11]1[CH2:12][CH2:13][C:14]1[C:15]3[C@:31]([CH3:39])([CH2:32][CH2:33][C:34]=12)[C@@H:18]([C@H:19]([CH3:30])[CH2:20][CH2:21][CH2:22][NH:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH2:17][CH:16]=3

Participants

3

Reactant 2

HCID 21887872Ethanol hydrochlorideHCID 694116633beta-tert-Butyldimethylsilyloxy-4,4-dimethyl-24-phenylamino-5alpha-chola-8,14-dien

Product 1

HCID 692839344,4-Dimethyl-24-phenylamino-5alpha-chola-8,14-dien-3beta-olYield 66.1%

Procedure

3β-tert-Butyldimethylsilyloxy-4,4-dimethyl-24-phenylamino-5α-chola-8,14-dien (100 mg) is hydrolysed with ethanol/HCl at 50° C. Aqueous work-up and crystallization from ethanol gives the title compound (53 mg). Melting point: 178-180° C. 1H-NMR (CDCl3, 300 MHz)): δ=7.19 (2H, t); 6.7 (1H, t); 6.63 (2H, d); 5.36 (1H, s); 3.6 (1H, s); 3.26 (1H, m); 3.1 (2H, m). MS: Calculated: 461.7. Found: 461.3.

Workup

  1. customAqueous work-up and crystallization from ethanol

Sources & evidence

ORD record
ord-29cd71583eb64745ba7d867a0d1a1376
Source dataset
uspto-grants-2002_06
Patent number
US06407086B2

Reaction notes

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