Formic Acid → HCID 90404956, compound

Participants

Reaction Steps

HCOOH (30.75 mL, 795 mmol) was added dropwise to a cooled (0° C.) solution of Et3N (41.0 mL, 318 mmol) in EtOAc (400 mL) while maintaining the temperature at 0° C. (R,R)—RuCl-TsDPEN (p-cymene) (100 mg, 0.2 mol %) was added to the reaction mixture followed by the addition of oxonitrile (3) (40.0 g, 159 mmol) and the reaction mixture was stirred at room temperature for 24 h. NaHCO3 (10%, 500 mL) was added and the mixture was extracted with EtOAc (500 mL). Organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give (R)-3-(3-(benzyloxy)phenyl)-3-hydroxypropanenitrile (4) as a pale yellow solid. Yield (38.0 g, 95%); 1H NMR (400 MHz, DMSO-d6) δ 7.46-7.44 (m, 2H), 7.41-7.37 (m, 2H), 7.33 (t, J=7.2 Hz, 1H), 7.26 (t, J=8.0 Hz, 1H), 7.07 (s, 1H), 6.99 (d, J=7.6 Hz, 1H), 6.92 (d, J=8.0 Hz, 1H), 5.95 (d, J=4.4 Hz, 1H), 5.09 (s, 2H), 4.86 (d, J=5.2 Hz, 1H), 2.90 (dd, J=16.8, 4.8 Hz, 1H), 2.80 (dd, J=16.8, 6.8 Hz, 1H).

Provenance & Evidence