تفاعل #59329

معادلة التفاعل

((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

المردود 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

المردود 76.0%

المذيبات

DMF

water

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheating
2. 2
   أخرىseparated
3. 3
   استخلاصthe aqueous phase extracted twice with each 10 ml ethyl acetate
4. 4
   تجفيفThe combine organic phases are dried over magnesium sulfate
5. 5
   أخرىevaporated to dryness

الإجراء التجريبي

((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+).

المصدر