Sodium Hydroxide → HCID 67341284, compound

Participants

Reaction Steps

(3R)-3-Cyano-1-(1,1-diphenylmethyl)pyrrolidine (0.70 g) was dissolved in tetrahydrofuran under an argon atmosphere. Titanium(IV) tetraisopropoxide (0.86 mL) and ethylmagnesium bromide (1.78 mL, 3 mol/L ether solution) were added to the solution at room temperature. After 05 h, trifluoroboron-diethyl ether complex (0.67 mL) was added dropwise to the mixture, and the resultant mixture was stirred at room temperature. After 18 h, 2 mol/L aqueous sodium hydroxide (30 mL) was added to the reaction mixture, and the resultant mixture was stirred for 0.25 hours. The product that precipitated was collected through filtration and then extracted. The formed aqueous layer was again extracted with ethyl acetate, and the organic layers were combined together, washed with saturated brine, and dried over sodium sulfate. The drying agent was removed through filtration, and the filtrate was concentrated under reduced pressure, to thereby yield crystals. The residue was subjected to silica gel chromatography, to thereby give the target compound (0.374 g, yield 48%).

Provenance & Evidence