Trifluoroacetic acid → HCID 86617380, compound

Participants

Reaction Steps

A solution of (3R)-N-{[2,4-dichlorophenyl]methyl}-N-(tetrahydro-2H-pyran-4-yl)-1-tert-butyloxycarbonylpyrrolidine-3-yl-methylamine (0.36 g, 0.81 mmol) in dichloromethane (10 ml) is stirred at room temperature with trifluoroacetic acid (0.93 g, 8.10 mmol) overnight. The reaction mixture is concentrated in vacuo and the oil is dissolved in methanol, purified using a SCX-2 column (10 g), then washed with methanol. The basic product elutes with methanolic ammonia (2M). Evaporation to an oil and further purification by preparative LC-MS gives a colourless oil. Dissolve the oil in isopropyl alcohol and add L-tartaric acid (1 eq) then heat to give a clear solution. Crystallise by cooling to give the title compound as a colourless solid. 1H NMR (300 MHz, DMSO) δH: 7.57-7.56 (2H, m), 7.44-7.40 (1H, m), 3.88-3.85 (4H, m), 3.70 (2H, s), 3.24-3.03 (5H, m), 2.77-2.70 (1H, m), 2.59-2.51 (2H, m), 2.44-2.31 (1H, m), 1.94-1.88 (1H, m), 1.66-1.48 (6H, m), LCMS: Rt=4.22 (12 min method) [M+H]=343/5.

Provenance & Evidence