Trifluoroacetic acid → HCID 66590906, compound

Participants

Reaction Steps

Cyclopent-2-enone (3.31 g, 40.4 mmol) and trifluoroacetic acid (0.031 mL, 0.404 mmol) were combined in dichloromethane (40 mL). 1-Methoxy-N-(3-(trifluoromethyl)benzyl)-N-((trimethylsilyl)methyl)methanamine (12.33 g, 40.4 mmol) from Step B was added as a solution in 10 mL of dichloromethane dropwise via addition funnel over 45 minutes at room temperature under nitrogen. The reaction was quenched with aqueous sodium bicarbonate and extracted with 2×100 mL of dichloromethane. The organic washes were combined and washed with brine. The solvent was removed in vacuo to give 2-(3-(trifluoromethyl)benzyl)hexahydrocyclopenta[c]pyrrol-4(5H)-one: 1H NMR (300 MHz, CDCl3) δ ppm 7.54-7.34 (m, 4H), 3.66 (d, J=13.4, 1H), 3.52 (d, J=13.4, 1H), 3.04 (dd, J=1.8, 8.9, 1H), 2.91 (ddd, J=2.8, 7.4, 11.7, 1H), 2.72-2.65 (m, 1H), 2.62 (d, J=8.9, 1H), 2.52-2.23 (m, 4H), 2.15 (ddd, J=8.1, 12.9, 17.1, 1H), 1.85-1.70 (m, 1H).

Provenance & Evidence