تفاعل #657330

ord-4aa473ed35c146d8b45c8845a529a8e4

معادلة التفاعل

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
المردود 104.5%
CC(C)(C)OC(=O)N1CCC(NC(=O)OCc2ccccc2)CC1
4-Benzyloxycarbonylamino-piperidine-1-carboxylic acid tert-butyl ester
المردود 104.5%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىthen partitioned between ethyl acetate (200 mL) and water (100 mL)
  2. 2
    أخرىThe organic layer was separated
  3. 3
    غسيلwashed with saturated brine solution (200 mL)
  4. 4
    تجفيفdried (MgSO4)
  5. 5
    ترشيحfiltered
  6. 6
    تركيزconcentrated

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09023843B2uspto-grants-2015_05