تفاعل #67704

معادلة التفاعل

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

المردود 62.0%

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

المردود 62.0%

المذيبات

methanol

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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)+].

المصدر