Reaction #1172

Reaction equation

4-Hydroxypiperidine

Et3N

benzyl chloroformate

CHCl3 MeOH

→

N-Cbz-piperidine

Yield 59.2%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   workup.ADDITIONwas added

Procedure

4-Hydroxypiperidine (10.8 g, 107 mmol) and Et3N (17 mL, 123 mmol) in 80 mL of CH2Cl2 was cooled in an ice bath whereupon benzyl chloroformate (16.3 mL, 114 mmol) was added. After stirring 1.5 h at R.T. the mixture was subjected to standard work-up conditions to give 13.9 g (55%) of N-Cbz-piperidine after chromatography (CHCl3 /MeOH; 10:1). [1H]-NMR(CDCl3) consistent with structure.

Source