반응 #59329

반응 방정식

((S)-6-Oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-carbamic acid tert-butyl ester

1,1,1-trifluoro-2,3-epoxypropane

1,1,1-trifluoro-2,3-epoxypropane

→

title compound

수율 76.0%

[(S)-5-(3,3,3-Trifluoro-2-hydroxy-propyl)-6-oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl ]-carbamic acid tert-butyl ester

수율 76.0%

용매

DMF

water

ethyl acetate

반응 조건

후처리

1. 1
   온도heating
2. 2
   기타separated
3. 3
   추출the aqueous phase extracted twice with each 10 ml ethyl acetate
4. 4
   건조The combine organic phases are dried over magnesium sulfate
5. 5
   기타evaporated to dryness

실험 절차

((S)-6-Oxo-6,7-dihydro-5H-dibenzo[b,d]azepin-7-yl)-carbamic acid tert-butyl ester (108 mg, 0.33 mmol) and 1,1,1-trifluoro-2,3-epoxypropane (762 mg, 6.7 mmol) were dissolved in DMF (2 ml) and heated to 90° C. for 4 h in a sealed tube. After addition of another 500 mg of 1,1,1-trifluoro-2,3-epoxypropane, heating was continued for 18 h. The mixture was diluted with ethyl acetate and water (10 ml each), separated and the aqueous phase extracted twice with each 10 ml ethyl acetate. The combine organic phases are dried over magnesium sulfate and evaporated to dryness. Chromatography (silica, eluent heptanes/ethyl acetate gradient from 1 to 30%) afforded the title compound as white solid (76%). MS: m/e=437(M+H+).

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