HCID 69212799, compound → HCID 67004890, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of (S)-1-(4-chlorobenzyl)-3-[N-{3(trifluoromethyl)benzoyl}glycyl]aminopyrrolidine (2.93 g, 6.66 mmol) and Pd(OH)2 in 5% HCO2H/methanol (70 mL) was stirred at 60° C. for 3 h. The Pd catalyst was filtered off through Celite, and the filtrate was concentrated. To the residue was added 2 N aqueous NaOH solution (100 mL) and the mixture was extracted with ethyl acetate (100 mL×3). The combined extracts were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography (SiO2, AcOEt/MeOH/Et3N=85/10/5-60/30/5) gave (S)-3-[N-{3(trifluoromethyl}benzoyl)glycyl]aminopyrrolidine (1.70 g, 81%) as an oil: 1H NMR (CDCl3, 270 MHz) δ 1.76 (d, J=7.3 Hz, 1 H), 2.07-2.25 (m, 1 H), 2.81-2.98 (m, 2 H), 3.02-3.11 (m, 2 H), 4.12 (s, 2 H), 4.41 (br, 1 H), 6.90 (br, 1 H), 7.45 (br, 1 H), 7.58 (dd, J=7.3 and 7.3 Hz, 1 H), 7.77 (d, J =7.3 Hz, 1 H), 8.02 (d, J=7.3 Hz, 1 H), 8.11 (s, 1 H); ESI/MS m/e 316.0 (M++H, C14H16F3N3O2).

Provenance & Evidence