반응 #67704

반응 방정식

trans-(4-Amino-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

intermediate G

trans-(4-Amino-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

Acetic acid

cyclopentanone

Sodium cyanoborohydride

→

title compound

수율 62.0%

trans-(4-Cyclopentylamino-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

수율 62.0%

용매

methanol

반응 조건

후처리

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued at 45° C. for 2 h
3. 3
   추출The mixture was extracted with 2N sodium carbonate solution and ethyl acetate
4. 4
   기타The combined organic phases were dried on sodium sulfate
5. 5
   여과filtered
6. 6
   기타evaporated
7. 7
   기타Purification of the residue by flash chromatography on silica gel (dichloromethane/methanol/ammonia 100:0:0→90:10:1)

실험 절차

trans-(4-Amino-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester (intermediate G, 1.0 g, 4.63 mmol) was dissolved in 90 mL methanol. Acetic acid (1.4 g, 23 mmol) and cyclopentanone (1.18 g, 14 mmol) were added and the reaction mixture was stirred at 45° C. overnight. Sodium cyanoborohydride (612 mg, 9.7 mmol) was added and stirring was continued at 45° C. for 2 h. The mixture was extracted with 2N sodium carbonate solution and ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and evaporated. Purification of the residue by flash chromatography on silica gel (dichloromethane/methanol/ammonia 100:0:0→90:10:1) yielded the title compound as a yellow solid (815 mg, 62%), MS: m/e=229.4 [(M-butene)+].

출처