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

Participants

Reaction Steps

Preparation according to Example 34: (+)-1-benzyl-3-(3-chloro-5-fluorophenyl)-pyrrolidin-3-ol (0.1 g, 0.33 mmol) iodoethane (1 mL, 12.37 mmol), dimethyl formamid (2 mL), morpholine (2 mL). Purification by flash chromatography on silica gel (ethyl acetate/methanol, 1:0 to 1:1). Yield: 0.05 g. [α]D=+16.7° (methanol). The amine was converted to the oxalic acid salt and recrystallized from ethanol/diisopropyl ether: M.p. 113-114° C.; MS m/z (relative intensity, 70 eV) 243 (M+, 6), 157 (7), 129 (11), 72 (33), 71 (bp).

Provenance & Evidence