Ethanol hydrochloride → 3beta-Hydroxy-4,4-dimethyl-24-(3-pentyl)-5alpha-chola-8,14-dien-24-one

HRID 1816484Notes

Reaction equation

HRID 1816484 reaction equation
CON(C)[C:4](=[O:38])[CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:26]2([CH3:27])[C:12]([C:13]3[CH2:14][CH2:15][C@@H:16]4[C@:21]([C:23]=3[CH2:24][CH2:25]2)([CH3:22])[CH2:20][CH2:19][C@H:18]([O:28][Si](C(C)(C)C)(C)C)[C:17]4([CH3:37])[CH3:36])=[CH:11][CH2:10]1)[CH3:8].[CH3:40][CH2:41][CH:42]([Mg]Br)[CH2:43][CH3:44].C(O)C.Cl>>[OH:28][C@H:18]1[CH2:19][CH2:20][C@@:21]2([CH3:22])[C@@H:16]([CH2:15][CH2:14][C:13]3[C:12]4[C@:26]([CH3:27])([CH2:25][CH2:24][C:23]=32)[C@@H:9]([C@H:7]([CH3:8])[CH2:6][CH2:5][C:4]([CH:42]([CH2:43][CH3:44])[CH2:41][CH3:40])=[O:38])[CH2:10][CH:11]=4)[C:17]1([CH3:37])[CH3:36]

Participants

4

Reactant 3

HCID 21887872Ethanol hydrochlorideHCID 878220303beta-tert-Butyldimethylsilyloxy-4,4-dimethyl-5alpha-chola-8,14-dien-24 oic acid-N-methoxy-N-methyl amideHCID 178456026HCID 178456026, compound

Product 1

HCID 694138453beta-Hydroxy-4,4-dimethyl-24-(3-pentyl)-5alpha-chola-8,14-dien-24-one

Procedure

3β-tert-Butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24 oic acid-N-methoxy-N-methyl amide (0.57 g) is reacted with 3-pentylmagnesiumbromide and hydrolysed with ethanol/HCl following the procedure outlined in example 6 to give the title compound (13 mg). 1H-NMR (CDCl3, 300 MHz): δ=5.35 (1H, s); 3.23 (1H, m). MS: Calculated: 454.7. Found: 454.3.

Sources & evidence

ORD record
ord-bbc3508ccbb74564b354c7d39c82e2f6
Source dataset
uspto-grants-2005_04
Patent number
US06884796B2

Reaction notes

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