Methyl chloroformate → HCID 67015385, compound

Participants

Reaction Steps

To a solution of 3-methoxycarbonyl-4-[3-(3-phenoxypropoxy)-4-methoxyphenyl]pyrrolidine (720 mg, 1.87 mmol) in 5 mL of CH2Cl2 at 0° C. was added DMAP (275 mg, 2.25 mmol), followed by methyl chloroformate (213 mg, 2.25 mmol). The solution was stirred for 2 hr, diluted with ether, and washed with 1M H3PO4. The aqueous layer was extracted with ether (2×) and ethyl acetate (1×). The combined organic layers were dried over MgSO4, filtered and concentrated to a colorless oil. Silica gel chromatography (4:2:1, hexanes:ethyl acetate:CH2Cl2) provided trans-1-methoxycarbonyl-3-methoxycarbonyl-4-[3-(3-phenoxypropoxy)-4-methoxyphenyl]pyrrolidine as a colorless oil (634 mg, 77%). Anal. Calcd for C24H29NO7 : C, 64.99; H, 6.59; N, 3.16. Found: C, 64.85; H, 6.57; N, 3.15.

Provenance & Evidence