Chlorotrimethylsilane → HCID 24956503, compound

HRID 1095570Notes

Reaction equation

HRID 1095570 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH2:7][CH:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:5][CH2:4]1.[Si]([Cl:34])(C)(C)C>C(OCC)(=O)C>[ClH:34].[CH3:29][N:2]([CH3:1])[C:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH2:7][CH:6]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 6397ChlorotrimethylsilaneHCID 24956504HCID 24956504, compound

Product 1

HCID 24956503HCID 24956503, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-[2-(4-Dimethylamino-4-phenylcyclohexyl)-1H-indol-3-yl]propionic acid (more polar diastereomer) (419 mg, 1.08 mmol) was dissolved in ethyl acetate (50 ml). Me3SiCl (276 μl, 1.16 mmol) was added dropwise at RT and the mixture was stirred for 16 h. The solvent was distilled off on a rotary evaporator and Example 153 (458 mg, m.p. 242-245° C., 100%) was obtained as a white solid.

Workup

  1. distillationThe solvent was distilled off on a rotary evaporator

Sources & evidence

ORD record
ord-e58be3b25fcc49fc9b8a42c0c09faff4
Source dataset
uspto-grants-2012_03
Patent number
US08138187B2

Reaction notes

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