반응 #48393

반응 방정식

Sodium hydride

tert-butyl (3R,6R)-2-oxo-6-phenylazepan-3-ylcarbamate

2-bromoethyl methyl ether

→

title compound

수율 86.3%

tert-Butyl (3R,6S)-1-(2-methoxyethyl)-2-oxo-6-phenylazepan-3-ylcarbamate

수율 86.3%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.ADDITIONAfter addition
2. 2
   기타the reaction was quenched with water
3. 3
   추출the mixture was extracted with ethyl acetate
4. 4
   세척The organic layer was washed with water (3×), saturated brine
5. 5
   건조dried over magnesium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated
8. 8
   기타Purification by silica gel chromatography (5% ethyl acetate/hexanes→30% ethyl acetate/hexanes)

실험 절차

Sodium hydride (60% dispersion in mineral oil; 6.2 mg, 0.158 mmol) was added to a solution of tert-butyl (3R,6R)-2-oxo-6-phenylazepan-3-ylcarbamate (40 mg, 0.131 mmol) and 2-bromoethyl methyl ether (0.013 mL, 0.138 mmol) in N,N-dimethylformamide (2 mL) at 0° C. After addition, the mixture was allowed to warm to ambient temperature. After 4 h, the reaction was quenched with water and the mixture was extracted with ethyl acetate. The organic layer was washed with water (3×), saturated brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (5% ethyl acetate/hexanes→30% ethyl acetate/hexanes) gave the title compound (41 mg). MS 363 (M+1).

출처