Methyl iodide → 3-(3-Chloro-5-fluorophenyl)-1-methylpyrrolidin-3-ol

Participants

Reaction Steps

Preparation according to Example 34: (−)-1-benzyl-3-(3-chloro-5-fluorophenyl)pyrrolidin-3-ol (0.115 g, 0.38 mmol) and iodomethane (1 mL, 15.9 mmol), dimethyl formamid (2 mL), morpholine (2 mL). Purification by flash chromatography on silica gel (ethyl acetate/methanol, 1:0 to 1:1). Yield: 0.1 g. [α]D=−21.7° (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) 229 (M+, 6), 129 (7), 109 (6), 58 (28), 57 (bp).

Provenance & Evidence