Chloride → 3beta-Hydroxy-4,4-dimethyl-5alpha-chola-8,14-dien-24-aldehyde

HRID 1816489Notes

Reaction equation

HRID 1816489 reaction equation
[CH3:1][C:2]1([CH3:28])[C@@H:24]([OH:25])[CH2:23][CH2:22][C@@:21]2([CH3:26])[C@H:3]1[CH2:4][CH2:5][C:6]1[C:7]3[C@:17]([CH3:27])([CH2:18][CH2:19][C:20]=12)[C@@H:10]([C@H:11]([CH3:16])[CH2:12][CH2:13][CH2:14][OH:15])[CH2:9][CH:8]=3.C(O)C(N)(CO)CO.[Cl-]>C1C=CC=CC=1>[OH:25][C@H:24]1[CH2:23][CH2:22][C@@:21]2([CH3:26])[C@@H:3]([CH2:4][CH2:5][C:6]3[C:7]4[C@:17]([CH3:27])([CH2:18][CH2:19][C:20]=32)[C@@H:10]([C@H:11]([CH3:16])[CH2:12][CH2:13][CH:14]=[O:15])[CH2:9][CH:8]=4)[C:2]1([CH3:1])[CH3:28]

Participants

5

Reactant 3

HCID 312ChlorideHCID 6503Tris(hydroxymethyl)aminomethaneHCID 155430924,4-Dimethyl-5alpha-chola-8,14-dien-3beta,24-diol

Product 1

HCID 155430943beta-Hydroxy-4,4-dimethyl-5alpha-chola-8,14-dien-24-aldehydeYield 61.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4,4-Dimethyl-5α-chola-8,14-dien-3β,24-diol (0.21 g) is dissolved in benzene (21 ml). Tris(triph chloride (1.04 g) is added and the mixture is stirred at room temperature for 20 hours. Purification by column chromatography gives the title compound (129 mg). 1H-NMR (CDCl3, 300 MHz): δ=9.79 (1H, s); 5.36 (1H, s); 1.05 (3H, s) 1.01 (3H, s); 0.95 (3H, d); 0.82 (3H, s); 0.80 (3H, s).

Workup

  1. customPurification by column chromatography

Sources & evidence

ORD record
ord-226ce6a2bef74cf0afb6e22414beafb4
Source dataset
uspto-grants-2005_04
Patent number
US06884796B2

Reaction notes

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