Water → tert-Butyl 3-[(propan-2-yl)amino]piperidine-1-carboxylate

Participants

Reaction Steps

A solution of tert-butyl 3-oxopiperidine-1-carboxylate (2 g, 10.03 mmol) and 2-aminopropane (710 mg, 12.04 mmol) in MeOH (40 mL) was stirred at rt for 1 h. To the solution was added NaBH4 (758 mg, 20.06 mmol) at 0° C. and the reaction mixture was stirred at rt for 12 h. The reaction mixture was diluted with ice-cooled water and the solvent was reduced to afford a residue which was dissolved in CH2Cl2 and washed with water. The organic layer was dried over Na2SO4, concentrated in vacuo and purified by column chromatography (silica gel, gradient MeOH in CH2Cl2) to afford the titled compound (2 g, 82%). 1H NMR (400 MHz, CDCl3): δ 4.01-3.90 (m, 1H), 3.78 (dt, J=3.6, 9.2 Hz, 1H), 3.48 (s, 1H), 2.96 (heptate, 0.1=6.4 Hz, 1H), 2.92-2.79 (m, 1H), 2.69-2.55 (m, 1H), 1.90-1.87 (m, 1H), 1.68-1.61 (m, 1H), 1.46 (s, 9H), 1.29-1.18 (m, 2H), 1.05 (d, J=6.0 Hz, 6H). ES-MS: m/z [M+1]=243.

Provenance & Evidence