N-methyl-2-pyrrolidone → HCID 86623625, compound

Participants

Reaction Steps

To a solution of methyl (R or S)-(5-Trifluoromethylsulfonyloxy-4-methyl-indan-1-yl)acetate (1.00 g, 2.84 mmol, from Step I) in N-methylpyrrolidinone (13 mL) under argon, zinc cyanide (267 mg, 2.27 mmol), Pd2 dba3 (13.0 mg, 14.2 μmol) and dppf (19.0 mg, 34.1 μmol) and the reaction mixture was heated to 100° C. After 16 hr, the reaction mixture was concentrated in vacuo and partitioned between EtOAc and H2O. The layers were separated and the organic layer was washed with H2O, brine and dried over MgSO4. The mixture was filtered, the filtrate concentrated in vacuo, and the residue purified by flash chromatography (5, 10% EtOAc/hexanes) on SiO2 to give 553 mg of the title compound as a white solid: 1H NMR (500 MHz, CDCl3) δ 1.76-1.80 (m, 1H), 2.41-2.50 (m, 5H), 2.73 (dd, 1H, J=5.8, 15.8 Hz), 2.78-2.84 (m, 1H), 2.91 (ddd, 1H, J=4.8, 8.7, 13.5 Hz) 3.61-3.67 (m, 1H), 3.71, (s, 3H), 7.07 (d, 1H, J=7.8 Hz), 7.43 (d, 1H, J=7.7 Hz).

Provenance & Evidence