Methyl iodide → tert-Butyl 3-(2-fluorobenzyl)-3-(methoxymethyl)piperidine-1-carboxylate

反応式

[H-].[Na+].[F:3][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[CH2:6][C:7]1([CH2:20][OH:21])[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.I[CH3:27]>C1COCC1>[F:3][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[CH2:6][C:7]1([CH2:20][O:21][CH3:27])[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:14])[CH2:8]1

参加物

実験手順

Sodium hydride (80 mg, 60% in mineral oil, 1.99 mmol) was added to a solution of tert-butyl 3-(2-fluorobenzyl)-3-(hydroxymethyl)piperidine-1-carboxylate (0.43 g, 1.33 mmol) in THF (5 ml) and the reaction mixture was stirred at room temperature for 20 mins. Iodomethane (0.125 ml, 1.99 mmoL) was added to the flask, and the reaction was allowed to stir at room temperature for 16 hrs. The reaction was quenched with water (5 ml) and was extracted using ethyl acetate (20 ml) three times. The ethyl acetate layers were combined, dried over sodium sulfate, filtered, and concentrated. The crude mixture was purified using flash chromatography (0-60% ethyl acetate in hexane) to give the titled compound (0.415 g).