Trifluoroacetic acid → HCID 86617385, compound

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Reaction Steps

Trifluoroacetic acid (1.5 ml, 15 mol, 10 eq) is added to a solution of tert-butyl (2S)-2-{[(3,5-dichlorobenzyl)(isobutyl)amino]methyl}pyrrolidine-1-carboxylate (0.611 g, 1.5 mmol, 1 eq) in dichloromethane (5 ml). After 16 hours if not complete by LCMS add an additional portion of trifluoroacetic acid (1.5 ml, 15 mol, 10 eq). After 72 hrs the solvent is removed in vacuo, methanol is added to the residue and the solution is loaded onto a SCX-2 (5 g) column. The column is washed with methanol (10 ml) and then the basic material is eluted with 2M ammonia in methanol (10 ml) and the solvent is removed in vacuo. The residue is dissolved in isopropanol (5 ml) and L-tartaric acid (1 eq) is added. The solution is heated to dissolve, then cooled and is left to stand in a fridge for 2 hrs, if no crystals have formed cyclohexane is added and the surface is scratched with a glass rod. The solid formed is filtered and dried in a vacuum oven at 60° C. for 16 hrs to give the N-(2-methylpropyl)-N-{[3,5-dichlorophenyl]-methyl}-(2S)-pyrrolidine-2-yl-methylamine L-Tartrate (0.23 g, 33%). 1H NMR (300 MHz, CD3OH) δH: 7.26 (3H, s) 4.29 (2H, s, tartrate) 3.44-3.78 (3H, m) 3.06-3.30 (4H, m) 2.42-2.71 (2H, m) 2.00-2.19 (3H, m) 1.83-1.99 (2H, m) 1.65-1.81 (1H, m) 1.46-1.64 (1H, m) 0.79 (6H, dd, J=6.5 and 3.2), LCMS: Rt=3.52 (12 min method) [M+H]=315.4.

Provenance & Evidence