Reacción #657330

ord-4aa473ed35c146d8b45c8845a529a8e4

Ecuación de reacción

O=C(Cl)OCc1ccccc1
benzyl chloroformate
CC(C)(C)OC(=O)N1CCC(N)CC1
4-amino-piperidine-1-carboxylic acid tert-butyl ester
O=C([O-])O.[Na+]
sodium bicarbonate
CC(C)(C)OC(=O)N1CCC(NC(=O)OCc2ccccc2)CC1
tan solid
Rendimiento 104.5%
CC(C)(C)OC(=O)N1CCC(NC(=O)OCc2ccccc2)CC1
4-Benzyloxycarbonylamino-piperidine-1-carboxylic acid tert-butyl ester
Rendimiento 104.5%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrothen partitioned between ethyl acetate (200 mL) and water (100 mL)
  2. 2
    OtroThe organic layer was separated
  3. 3
    Lavadowashed with saturated brine solution (200 mL)
  4. 4
    Secadodried (MgSO4)
  5. 5
    Filtraciónfiltered
  6. 6
    Concentraciónconcentrated

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09023843B2uspto-grants-2015_05