tert-Butyl(4-chlorobutoxy)dimethylsilane → HCID 59201333, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1)=[O:6].[C:23]([Si:27]([O:30][CH2:31][CH2:32][CH2:33][CH2:34]Cl)([CH3:29])[CH3:28])([CH3:26])([CH3:25])[CH3:24]>C1COCC1>[Si:27]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][C@:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[CH2:8]1)([C:4]1[CH:20]=[CH:21][CH:22]=[C:2]([Cl:1])[CH:3]=1)[OH:6])([C:23]([CH3:24])([CH3:25])[CH3:26])([CH3:28])[CH3:29]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of (R)-tert-butyl 3-(3-chlorobenzoyl)piperidine-1-carboxylate (1.62 g, 5 mmol) in anhydrous THF (20 mL) under N2 was cooled in a dry ice-acetone bath. The Grignard reagent derived from tert-butyl-(4-chloro-butoxy)-dimethyl-silane (50 mL) prepared above was added dropwise. After addition, the mixture was allowed to warm to rt and stirred for 2 h (monitored by tlc). The reaction was quenched with satd aq NH4Cl (70 mL) and extracted with EtOAc (3×40 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with 10:90 EtOAc/hexane to afford (R)-tert-butyl 3-((S)-5-(tert-butyldimethylsilyloxy)-1-(3-chlorophenyl)-1-hydroxypentyl)piperidine-1-carboxylate (1.65 g, 65%). 1H NMR (400 MHz, CDCl3): 0.02 (s, 6H), 7.30 (d, 2H), 0.85 (s, 9H), 1.47 (s, 9H), 1.92 (m, 3H), 2.52 (m, 3H), 3.56 (m, 2H), 3.63 (m, 2H), 3.97-4.21 (m, 2H), 4.36 (m, 1H), 7.16-7.25 (m, 3H), 7.36 (m, 1H). MS (E/Z): 512 (M+H+)