tert-Butyl 4-formylpiperidine-1-carboxylate → tert-Butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of N-tert-butoxycarbonyl-4-piperidinecarboxaldehyde (32.20 g, 151.45 mmol) in tetrahydrofuran at −78° C. is added methyl magnesium bromide (2 M in diethyl ether, 100.96 mL, 302.89 mmol). The reaction is stirred at −78° C. for 4.5 h, and then warmed to −50° C. for 30 min. The reaction is quenched with water at −50° C. and allowed to warm to room temperature for 16 h. The solvents are removed and the material is partitioned between diethyl ether and 0.1 M hydrochloric acid. The mixture is extracted with diethyl ether. The combined organic layers are washed with 0.1 M hydrochloric acid, saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated to dryness. The crude is purified by flash chromatography over silica gel to afford 16.90 g of the title compound as a colourless oil. MS (m/z) 229 (M+1).

Provenance & Evidence