Reacción #1350602

Ecuación de reacción

tert-Butyl (3S)-3-benzyloxycarbonylamino-2-oxoperhydroazepine-1-acetate

→

tert-butyl (3S)-3-amino-2-oxoperhydroazepine-1-acetate

Rendimiento 79.7%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Otropurged with argon
2. 2
   workup.ADDITION10% palladium or carbon (1.5 g) was added
3. 3
   Otrothe flask evacuated
4. 4
   workup.ADDITIONfilled with hydrogen from a balloon
5. 5
   OtroThe reaction mixture was then purged with argon
6. 6
   Filtraciónfiltered through diatomaceous earth
7. 7
   OtroThe filtrate was evaporated

Procedimiento

tert-Butyl (3S)-3-benzyloxycarbonylamino-2-oxoperhydroazepine-1-acetate (15 g) was disolved in ethanol (150 ml) and purged with argon. 10% palladium or carbon (1.5 g) was added and the flask evacuated and filled with hydrogen from a balloon. The reaction mixture was stirred at ambient temperature for 4 hours. The reaction mixture was then purged with argon and filtered through diatomaceous earth. The filtrate was evaporated to give tert-butyl (3S)-3-amino-2-oxoperhydroazepine-1-acetate (7.7 g) as a viscous oil; NMR (CDCl3): 1.45 (s, 9H), 1.55-2.05 (m, 6H), 3.2-3.3 (d, 1H), 3.55-3.75 (two overlapping doublets, 2H), 3.95-4.25 (q, 2H); mass spectroscopy, m/e (ES+) 243.2 (MH+).

Fuente