Reaction #657330

Reaction equation

benzyl chloroformate

4-amino-piperidine-1-carboxylic acid tert-butyl ester

sodium bicarbonate

→

tan solid

Yield 104.5%

4-Benzyloxycarbonylamino-piperidine-1-carboxylic acid tert-butyl ester

Yield 104.5%

Solvents

THF

Conditions

Workup

1. 1
   Otherthen partitioned between ethyl acetate (200 mL) and water (100 mL)
2. 2
   OtherThe organic layer was separated
3. 3
   Washwashed with saturated brine solution (200 mL)
4. 4
   Dryingdried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated

Procedure

To a solution of 4-amino-piperidine-1-carboxylic acid tert-butyl ester (11.98 g, 58.4 mmol, 1 equiv) in THF (80 mL) at 23° C. was added a saturated solution of sodium bicarbonate (200 mL) followed by benzyl chloroformate (9.19 mL, 64.2 mmol, 1.1 equiv). The reaction was stirred for 55 min then partitioned between ethyl acetate (200 mL) and water (100 mL). The organic layer was separated, washed with saturated brine solution (200 mL), dried (MgSO4), filtered and concentrated to give 20.4 g of tan solid. This material was used in the next step without further purification.

Source