Triethylamine → (S)-1-Cbz-3-Boc-Aminopiperidine

Participants

Reaction Steps

To a solution of tert-butyl(S)-piperidin-3-ylcarbamate (1.0 g, 5.0 mmol) and Et3N (0.76 mL) in CH2Cl2 was added Cbz-Cl (50% solution in toluene, 5.49 mmol, 0.78 mL) at 0° C. The reaction mixture was then warmed to rt and stirred for 3 h, diluted with CH2Cl2 (50 mL) and washed with water (3×5 mL). The organic layer was then dried over Na2SO4 and concentrated in vacuo to give (1.5 g, 89%) of the titled compound which was used without further purification. 1H NMR (400 MHz, CDCl3): δ 7.35-7.38 (m, 5H), 5.13-5.12 (d, 2H), 4.61 (bs, 1H), 3.73-3.67 (m, 2H), 3.51-3.46 (m, 2H), 3.26-2.23 (m, 2H), 1.86-1.80 (m, 2H), 1.66-1.50 (m, 1H), 1.42 (s, 9H). LC-MS: m/z [M-100]=235 & [M+23]=357.

Provenance & Evidence