Potassium Carbonate → HCID 24853223, compound

Participants

Reaction Steps

To a stirred solution of 1-[4-(3-aminotricyclo[3.3.1.03,7]non-1-yl)phenyl]pyrrolidin-2-one obtained in step II (0.36 g, 1.2 mmol) in DMSO (4.8 mL) at an ice bath temperature under nitrogen atmosphere was added K2CO3 (0.48 g, 3.6 mmol) followed by addition of (2S)-1-(chloroacetyl)pyrrolidine-2-carbonitrile (0.21 g, 1.2 mmol). After stirring the reaction mixture at r.t for 3 h, it was diluted with EtOAc and washed with water and brine, dried over Na2SO4, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography to obtain the title compound (2S)-1-{N-[2-[4-(2-oxopyrrolidin-1-yl)phenyl]hexahydro-2,5-methanopentalen-3a(1H)-yl]glycyl}pyrrolidine-2-carbonitrile as a white solid (0.26 g) in 50% yield. M.R: 254-256° C.; m/z (M+1) 433; 1H NMR (300 MHz, CDCl3) δ: 7.54 (d, J=8.5 Hz, 2H), 7.23 (d, J=8.5 Hz, 2H), 4.30-4.20 (m, 1H), 4.06-4.18 (m, 2H), 3.87 (t, J=7.0 Hz, 1H), 3.80-3.50 (m, 4H), 2.64 (t, J=7.8 Hz, 2H), 2.58-1.60 (m, 18H).

Provenance & Evidence