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

Participants

Reaction Steps

To a solution of (S)-tert-butyl piperidin-3-ylcarbamate (5 g, 24.9 mmol) and Et3N (3.8 mL, 27.4 mmol) in CH2Cl2 (75 mL) was added Cbz-Cl (3.92 mL, 27.4 mmol) at 0° C., after the addition was complete the reaction was warmed to rt and stirred for 4 h. The reaction was diluted with ice cooled water (30 mL) and the CH2Cl2 layer was separated and dried over Na2SO4 and concentrated in vacuo to give (7.5 g, 89%) of the tilted compound. 1H NMR (400 MHz, CDCl3): δ 7.40-7.24 (m, 5H), 5.18 (s, 2H), 4.58 (bs, 1H), 3.80-3.62 (m, 2H), 3.55-3.41 (m, 1H), 3.37-3.21 (m, 2H), 1.82-1.78 (m, 1H), 1.75-1.69 (m, 1H), 1.61-1.53 (m, 2H), 1.42 (s, 9H). ES-MS: m/z [M+1]=335.

Provenance & Evidence