反应详情

A solution of 372 mg (1 mmol) of tert-butyl (3RS,4RS)-4-carbamimidoyl-3-hydroxy-piperidine-1-carboxylate acetate in 10 ml of methanol was treated with 1 ml of 1N sodium methylate solution and stirred at room temperature. Subsequently,205 mg (1 mmol) of 2-benzyloxy-3-dimethylamino-acrolein (EPA 0 477 901) were added thereto and the solution was heated to reflux for 18 hours. For the working-up, the reaction mixture was evaporated under reduced pressure and the residue was taken up in 20 ml of methylene chloride and washed with 5 ml of water. The organic phase was separated, dried over sodium sulphate and finally evaporated under reduced pressure. For purification, the residue was chromatographed on silica gel using a 1:4 mixture of methylene chloride and ethyl acetate as the eluent. There were obtained 106 mg (27% of theory) of tert-butyl (3RS,4RS)-4-(5-benzyloxy-pyrimidin-2-yl)-3-hydroxy-piperidine-1-carboxylate as a colourless oil; MS: 386 (M+H)+.

1. temperaturethe solution was heated
2. temperatureto reflux for 18 hours
3. customthe reaction mixture was evaporated under reduced pressure
4. washwashed with 5 ml of water
5. customThe organic phase was separated
6. dry with materialdried over sodium sulphate
7. customfinally evaporated under reduced pressure
8. customFor purification
9. customthe residue was chromatographed on silica gel using
10. additiona 1:4 mixture of methylene chloride and ethyl acetate as the eluent