Benzyl chloroformate → HCID 58303515, compound

Participants

Reaction Steps

A solution of ((3R,4R)-1-Benzyl-4-fluoromethyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester (1 g, 3.24 mmol) in methanol (20 mL) was hydrogenated at 1 atm with 10% palladium on carbon (100 mg) for 24 hours. He crude reaction mixture was filter through celite then concentrate to an oil. The crude amine was dissolved in dichloromethane (8 ml) then cooled to 0 C and diisopropylethylamine (619 ul, 3.57 mmol) was added followed by benzyl chloroformate (507 ul, 3.57 mmol, 1.1 equiv.). The crude reaction was concentrated to an oil then purified by silica gel chromatography eluting with 0-20% EtOAc in Heptane which gave the title compound IXa of as a colorless oil (811 mg). 1H NMR (400 MHz, CHLOROFORM-d) 1.45 (s, 9H) 2.67 (br. s., 1H) 3.24-3.49 (m, 2H) 3.63-3.80 (m, 2H) 4.27-4.53 (m, 2H) 4.53-4.66 (m, 1H) 4.70 (dd, J=9.73, 4.93 Hz, 1H) 5.14 (br. s., 2H) 7.37 (br. s., 5H); LCMS: M+1−Boc=253.

Provenance & Evidence