Diisopropylethylamine → (2S,3R)-2-(3-Chloro-2-fluoro-benzylcarbamoyl)-3-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

The mixture of (2S,3R)-3-methoxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (60.0 mg, 0.245 mmol), (3-chloro-2-fluorophenyl)methanamine (0.034 mL, 0.269 mmol), HBTU (139 mg, 0.367 mmol) and DIPEA (0.085 mL, 0.489 mmol) in CH2Cl2 (5 mL) was stirred for 20 h at RT. The reaction mixture was then diluted with CH2Cl2, and the organics were washed subsequently with 0.1N aqueous HCl (3×), aqueous NaHCO3 solution (2×) and brine. The organic layers were dried (Phase separator), concentrated in vacuo and the residue was purified by preparative HPLC (Waters Sunfire, C18-ODB, 5 μm, 30×100 mm; flow: 40 mL/min; eluent: 5-100% CH3CN/H2O for 20 min, 100% CH3CN for 2 min, CH3CN and H2O containing 0.1% TFA) to afford the title compound as a white solid. MS (LC/MS): 387 [M+H]+, 331 [MH−tBu]+, 287 [MH−Boc]+; tR (HPLC conditions b): 4.26 min.

Provenance & Evidence