Reacción #44480

Ecuación de reacción

N-(tert-butoxycarbonyl)-hexahydro-1H-azepin-4-one

O-benzylhydroxylamine hydrochloride

ammonium acetate

→

title compound

4-Amino-azepane-1-carboxylic acid tert-butyl ester

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe solvent was evaporated in vacuo
2. 2
   Otrothe crude oxime was purified by flash column chromatography (hexanes:ethyl acetate 100:0 to 50:50)
3. 3
   workup.ADDITIONadded 10% by weight Pd/C (100 mg)
4. 4
   FiltraciónThe reaction was filtered through a pad of celite and filtrate
5. 5
   Otroevaporated in vacuo

Procedimiento

A solution of N-(tert-butoxycarbonyl)-hexahydro-1H-azepin-4-one (0.5 g, 2.34 mmoles), O-benzylhydroxylamine hydrochloride (0.41 g, 2.57 mmoles) and ammonium acetate (0.45 g, 5.86 mmoles) in methanol (10 mL) was refluxed for 1.2 hours. The solvent was evaporated in vacuo and the crude oxime was purified by flash column chromatography (hexanes:ethyl acetate 100:0 to 50:50). The product was taken in 4N NH3 in methanol (10 mL) and added 10% by weight Pd/C (100 mg) and stirred over H2 at balloon pressure for twelve hours. The reaction was filtered through a pad of celite and filtrate evaporated in vacuo to provide the title compound.

Fuente