Dimethylformamide → HCID 90386983, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl trans-3-((3-chloroisoquinolin-1-yl)oxy)-4-methylpyrrolidine-1-carboxylate (1 g, 2.76 mmol), zinc cyanide (0.647 g, 5.51 mmol), Pd(PPh3)4 (0.318 g, 0.276 mmol) and DMF (7.83 mL) was heated in a microwave reactor at 160° C. for 20 minutes. The reaction mixture was subsequently taken up in EtOAc (100 mL), washed with brine (50 mL) and water (50 mL), dried over Na2SO4, and concentrated onto silica gel. The crude product was purified by flash column chromatography (SiO2) eluting with a 5-50% gradient of heptane in EtOAc to give title compound as a white solid (0.796 g, 82%). 1H NMR (500 MHz, CDCl3) δ ppm 1.17 (d, 3H), 1.41-1.54 (m, 9H), 2.60 (br s, 1H), 3.26 (br s, 1H), 3.45-3.65 (br s, 1H), 3.74 (br s, 1H), 3.93 (dd, 1H), 5.40 (dt, 1H), 7.67-7.87 (m, 4H), 8.27 (d, 1H); ESI-MS m/z [M+H-tert-butyl]+ 298.6.

Provenance & Evidence