Water → HCID 59201599, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-tert-butyl 3-((R)-1-(2-aminoethoxy)-1-(3-chlorophenyl)butyl)piperidine-1-carboxylate (410 mg, 1 mmol) and DMAP (61 mg, 0.5 mmol) in dry CH2Cl2 (3 mL), Et3N (303 mg, 3 mmol) was added. The resulting mixture was cooled to 0-5° C. using a ice-water bath, a solution of methyl chloroformate (472 mg, 5 mmol) in dry CH2Cl2 (2 mL) was added dropwise. After addition, the reaction mixture was stirred for 1-2 h at 0-5° C. Upon completion of the reaction water (5 mL) was added and the aqueous layer was extracted with CH2Cl2 (3×15 mL). The combined organic layers were washed with 10% citric acid (2×10 mL) and brine, then dried over Na2SO4, filtered and concentrated to afford (R)-tert-butyl 3-((R)-1-(3-chlorophenyl)-1-(2-(methoxycarbonylamino)ethoxy)butyl)piperidine-1-carboxylate (460 mg, 98%), which was used in the next step without further purification.

Provenance & Evidence