Iodoethane → 3-(3-Chloro-5-fluorophenyl)-1-ethylpyrrolidin-3-ol

Participants

Reaction Conditions

Reaction Steps

A mixture of (−)-1-benzyl-3-(3-chloro-5-fluorophenyl)pyrrolidin-3-ol (0.66 g, 2.16 mmol) and iodoethane (4 mL, 50.2 mmol) was refluxed for 4 h. The mixture was evaporated and tert-butyl methyl ether (20 mL) was added. The solvent was decantated off, morpholine (5 mL) was added and the mixture was heated under microwave irradiation at 120° C. for 30 minutes. The mixture was evaporated and purified twice by flash chromatography on silica gel (methanol/ethyl acetate, 7:3 to 3:7 and isocratic 1:1) to give the title compound (0.26 g). [α]D=−21.4° (methanol). The amine was converted to the oxalic acid salt and recrystallized from ethanol/diethyl ether/diisopropyl ether: M.p. 117-118° C.; MS m/z (relative intensity, 70 eV) 243 (M+, 23), 157, (78), 130 (82), 129 (95), 71 (bp).

Provenance & Evidence