Aluminium lithium hydride → 3-Benzylamino-4-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of LiAlH4 (2M in THF, 14 mmol in 25 ml THF), cooled to 0° C., was slowly added a solution of 3-benzylamino-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (4.53 g, 12.5 mmol) in THF (25 mL). The reaction mixture was stirred at 0° C. for 15 min and then at room temperature for 2 h. The reaction mixture was again cooled to 0° C. and quenched with Na2SO4, 10 H2O and stirred for 16 h. The reaction mixture was filtered, washed with THF and concentrated to yield title compound (3.69 g, 92%). MS (ESI) mass calcd. for C18H28N2O3, 320.43; m/z found, 321.3 [M+H]+. 1H NMR (CDCl3): 7.42-7.19 (m, 5H), 5.64-4.97 (m, 1H), 4.57-4.0 (m, 1H), 3.99-3.82 (m, 2H), 3.79-3.56 (m, 3H), 3.04-2.58 (m, 3H), 1.95-1.79 (m, 2H), 1.74-1.55 (m, 2H), 1.47 (s, 9H).

Provenance & Evidence