Allyl bromide → (+)-1-Allyl-3-(2,3-difluorophenyl)pyrrolidin-3-OL

Participants

Reaction Steps

Preparation according to Example 8: Enantiomer E2 of 3-(2,3-difluorophenyl)pyrrolidin-3-ol (0.5 g, 2.5 mmol), acetonitrile (20 mL), potassium carbonate (0.69 g, 5 mmol) and 3-bromo-1-propene (0.23 mL, 2.78 mmol). Refluxed for 2 h. Purification by flash chromatography on silica gel (ethyl acetate/methanol, 5:1). Yield: 0.33 g. [α]D=−26.6° (methanol). The amine was converted to the oxalic acid salt and recrystallized from methanol/diisopropyl ether: M.p. 120° C.; MS m/z (relative intensity, 70 eV) (239 (M+, 25), 198 (48), 141 (35), 127 (23), 83 (bp).

Provenance & Evidence