Allyl bromide → HCID 25143955, compound

Participants

Reaction Conditions

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 allylbromide (0.13 mL, 1.59 mmol) was heated at 60° C. for 2 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, 7:1) gave the title compound (0.08 g). [α]D=−20.3° (methanol). The amine was converted to the oxalic acid salt and recrystallized from ethanol/diisopropyl ether: M.p. 102-103° C.; MS m/z (relative intensity, 70 eV) 239 (M+, 22), 83 (bp), 198 (52), 82 (33), 84 (29), 113 (27).

Provenance & Evidence