반응 #71879

반응 방정식

Methanol

hydrochloric acid ethyl acetate

tert-butyl cis(±)-4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidine-1-carboxylate

tert-Butyl cis(±)-4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidine-1-carboxylate

Trimethylsilyl isocyanate

→

title compound

수율 81.0%

cis(±)-Benzyl (1-carbamoyl-3-methoxypiperidin-4-yl)carbamate

수율 81.0%

용매

ethyl acetate

반응 조건

후처리

1. 1
   기타the solvent was evaporated under reduced pressure
2. 2
   workup.ADDITIONThe residue was diluted with dichloromethane
3. 3
   세척washed with a 1 N aqueous sodium hydroxide solution and brine
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   농축concentrated under reduced pressure
6. 6
   workup.STIRRINGthe mixture was stirred at room temperature for 15 hours
7. 7
   workup.STIRRINGby stirring for 30 minutes
8. 8
   여과The precipitated solid was filtered off
9. 9
   세척washed with dichloromethane

실험 절차

A 4 N hydrochloric acid/ethyl acetate solution (30 ml, 120 mmol) was added to a solution of tert-butyl cis(±)-4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidine-1-carboxylate obtained in Example (103a) in ethyl acetate (10 mL). The mixture was stirred for 45 minutes and the solvent was evaporated under reduced pressure. The residue was diluted with dichloromethane, washed with a 1 N aqueous sodium hydroxide solution and brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. Trimethylsilyl isocyanate (0.86 g, 7.5 mmol) was added to the resulting residue, and the mixture was stirred at room temperature for 15 hours. Methanol (1 mL) was added, followed by stirring for 30 minutes. The precipitated solid was filtered off and washed with dichloromethane to obtain 1.44 g of the title compound as a colorless solid (81%).

출처