تفاعل #44480

معادلة التفاعل

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

O-benzylhydroxylamine hydrochloride

ammonium acetate

→

title compound

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

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   أخرىThe solvent was evaporated in vacuo
2. 2
   أخرىthe 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
   ترشيحThe reaction was filtered through a pad of celite and filtrate
5. 5
   أخرىevaporated in vacuo

الإجراء التجريبي

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.

المصدر