Reaktion #67704

Reaktionsgleichung

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

Ausbeute 62.0%

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

Ausbeute 62.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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)+].

Quelle