Acetonitrile → HCID 25143956, compound

Participants

Reaction Steps

In a sealed tube a mixture of enantiomer E2 of 3-(3,5-difluorophenyl)pyrrolidin-3-ol (0.29 g, 1.45 mmol), acetonitrile (15 mL), potassium carbonate (0.4 g, 2.9 mmol) and 2-bromoethylmethyleter (0.145 mL, 1.55 mmol) was stirred at ambient temperature for 4 h. and then at 80° C. for 1 h. Aqueous sodium carbonate (10%, 5 mL) was added and the aqueous phase was extracted with ethyl acetate (2×50 mL). The combined organic phase was dried (Na2SO4) and evaporated. Purification by flash chromatography on silica gel (ethyl acetate/methanol, 10:1) gave the title compound (0.157 g). [α]D=−18.9° (methanol). The amine was converted to the oxalic acid salt and recrystallized from ethanol/diisopropyl ether: M.p. 130-131° C.; MS m/z (relative intensity, 70 eV) 257 (M+, 2), 212 (bp), 182 (52), 127 (12), 213 (12), 58 (8).

Provenance & Evidence