Aniline → 3beta-tert-Butyldimethylsilyloxy-4,4-dimethyl-24-phenylamino-5alpha-chola-8,14-dien

HRID 1816486Notes

Reaction equation

HRID 1816486 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C@@H:11]([CH2:12][CH2:13][C:14]3[C:15]4[C@:26]([CH3:34])([CH2:27][CH2:28][C:29]=32)[C@@H:18]([C@H:19]([CH3:25])[CH2:20][CH2:21][C:22](O)=O)[CH2:17][CH:16]=4)[C:10]1([CH3:36])[CH3:35])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Si:1]([O:8][C@H:9]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C@@H:11]([CH2:12][CH2:13][C:14]3[C:15]4[C@:26]([CH3:34])([CH2:27][CH2:28][C:29]=32)[C@@H:18]([C@H:19]([CH3:25])[CH2:20][CH2:21][CH2:22][NH:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:17][CH:16]=4)[C:10]1([CH3:35])[CH3:36])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6115AnilineHCID 21226445Aluminium lithium hydrideHCID 694107953beta-Tert-butyidimethylsilyloxy-4,4-dimethyl-5alpha-chola-8,14-dien-24 oic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3β-tert-Butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24 oic acid (0.15 g) is reacted with aniline following the procedure outlined in example 10 and reduced with lithium aluminium hydride (0.15 g) in THF at room temperature. Aqueous work-up and crystallization from methanol gives 3β-tert-butyldimethylsilyloxy-4,4-dimethyl-24-phenylamino-5α-chola-8,14-dien (106 mg). 1H-NMR (CDCl3, 300 MHz)): δ=7.17 (2H, t); 6.69 (1H, t); 6.6 (2H, d); 5.35 (1H, s); 3.6 (1H, s); 3.2 (1H, m); 3.09 (2H, m); 0.9 (9H, s); 0.04 (6H, m).

Workup

  1. customAqueous work-up and crystallization from methanol

Sources & evidence

ORD record
ord-e536b6abb53f43a199131a0aa9617387
Source dataset
uspto-grants-2005_04
Patent number
US06884796B2

Reaction notes

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