反应详情

To a suspension of 4-cyclohexyl-4-[(4,4-dimethyl-2-oxo-1,3-oxazolidin-3-yl)methyl]piperidinium chloride (150 mg; 0.4532 mmol) in methylene chloride (4.0 mL) was added N-methylmorpholine (183 mg; 0.2 mL). After 20 min, the following reagents were added sequentially: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (130 mg; 0.6798 mmol), 1-hydroxybenzotriazole (92 mg; 0.6798 mmol) and the product of step D (154 mg; 0.4985 mmol). The final reaction mixture was maintained at ambient temperature for 48 h. The reaction mixture was diluted with methylene chloride (100 mL) followed by washing the organic solution with saturated sodium bicarbonate and brine. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo to provide the crude N-BOC protected pyrrolidine that was purified on silica gel (50% ethyl acetate/hexane as the elution solvent). The crude N-BOC protected pyrrolidine was then dissolved in ethyl acetate (2 mL) followed by the addition of a saturated solution of hydrogen chloride in ethyl acetate (2 mL). The reaction mixture was maintained at ambient temperature for 2 h at which time the volatiles were removed in vacuo. The crude product was triturated to high purity with diethyl ether which furnished 204 mg of the title compound as a hydrochloride salt.

1. additionthe following reagents were added sequentially
2. customThe final reaction mixture
3. washby washing the organic solution with saturated sodium bicarbonate and brine
4. dry with materialThe organic phase was dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto provide the crude N-BOC
8. customwas purified on silica gel (50% ethyl acetate/hexane as the elution solvent)
9. dissolutionwas then dissolved in ethyl acetate (2 mL)
10. additionfollowed by the addition of a saturated solution of hydrogen chloride in ethyl acetate (2 mL)
11. temperatureThe reaction mixture was maintained at ambient temperature for 2 h at which time the volatiles
12. customwere removed in vacuo
13. customThe crude product was triturated to high purity with diethyl ether which