4-Methylmorpholine → HCID 21018571, compound

Participants

Reaction Steps

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.

Provenance & Evidence