Formic Acid → HCID 90406331, compound

Participants

Reaction Steps

The solution of Et3N (0.78 g, 7.6 mmol) in EtOAc (50 mL) was cooled to 0° C. for 15 min. HCOOH (0.88 g, 19 mmol) was added dropwise to the reaction mixture and the solution was stirred for 20 min at same temperature. The solution of 0.2 mol % (R,R)RuCl-TsDPEN(p-cymene) (10 mg) in EtOAc was added to the reaction mixture, followed by addition of ketonitrile (13) (1.0 g, 3.8 mmol) in EtOAc at 0° C. The reaction mixture was stirred for 18 h at rt. After completion of the reaction (as monitored by TLC) the reaction mixture was diluted with water, extracted with EtOAc, dried over anhydrous Na2SO4, and concentrated under reduced pressure. Purification by column chromatography (100-200 silica mesh, 20-25% EtOAc in hexanes) gave (R)-3-hydroxy-3-(3-((tetrahydro-2H-pyran-4-yl)methoxy)phenyl)propanenitrile (14) as a white solid. Yield (0.75 g, 75%); 1H NMR (400 MHz, DMSO-d6) δ 7.24 (t, J=8.0 Hz, 1H), 6.98-6.95 (m, 2H), 6.83 (dd, J=8.0, 4.0 Hz, 1H), 5.92 (d, J=4.8 Hz, 1H), 4.85 (dd, J=11.2, 4.8 Hz, 1H), 3.89-3.81 (m, 4H), 3.35-3.30 (m, 2H), 2.84 (dq, J=16.8, 4.8 Hz, 2H), 2.04-1.96 (m, 1H), 1.69-1.66 (m, 2H), 1.37-1.27 (m, 2H).

Provenance & Evidence