Triethylamine → HCID 68581004, compound

Participants

Reaction Conditions

Reaction Steps

4-[3-[1, 3]-Dioxolan-2-yl-1-(4-fluorophenyl)-1-hydroxypropyl-]3-hydroxymethylbenzonitrile (15 g) was dissolved in dichloromethane (150 mL) at room temperature, followed by addition of triethylamine (25 mL). The reaction mixture was cooled to 5-10° C. and stirred for 5 min, followed by addition of methane sulfonylchloride (8.4 g). The reaction mixture was warmed to room temperature and stirred for 10 min. It was quenched with 2% NaOH (100 mL) while maintained to 10-20° C. The organic phase was separated and was dissolved in water and concentrated to give 19.2 g crude product. 1H NMR (CDCl3, δ): 1.42-1.57 (m, 1H), 1.63-1.76 (m, 1H), 2.20-2.38 (m, 2H), 3.78-3.96 (m, 4H), 4.84 (t, J=3 Hz, 1H), 5.18 (m, 2H), 7.00 (m, 2H), 7.38-7.50 (m, 4H), 7.60 (m, 1H). The product was separated into its enantiomers by CHIRALCEL OD=column using Methanol as eluent. Enantiomer 6a, 6.67 min; Enantiomer 6b, 8.30 min.

Provenance & Evidence