Trifluoroacetic acid → HCID 69063812, compound

Participants

Reaction Steps

To a stirred solution of 1,1-dimethylethyl (3R)-3-((3R)-tetrahydrofuran-3-yl{[2-(trifluoromethyl)phenyl]-methyl}amino)pyrrolidine-1-carboxylate (0.12 g, 0.29 mmol) in dichloromethane (4 mL) was added trifluoroacetic acid (2 mL). After stirring at room temperature for 3 h the solvent was removed in vacuo and the crude product taken up in methanol. This solution was absorbed onto a cationic ion exchange resin (Isolute™ SCX-2) and the basic components recovered from the column by elution with 2N ammonia in methanol. The eluate was evaporated, taken up again in methanol and L-tartaric acid (1 equivalent) added. The solvent was removed in vacuo and the resultant gum triturated with diethyl ether to yield the title compound as a pink microcrystalline solid. 1H NMR (300 MHz, CD3OD) δH: 7.82 (d, 1H), 7.57 (d, 1H), 7.53 (t, 1H), 7.32 (t, 1H), 4.31 (s, 2H), 3.92-3.82 (m, 3H), 3.70-3.47 (m, 5H), 3.37-3.22 (m, 2H), 3.17-3.03 (m, 1H), 2.94 (dd, 1H), 2.12-1.96 (m, 2H), 1.85-1.67 (m, 2H); MS: [M+H]=315.

Provenance & Evidence