1-Bromo-2-methylpropane → (-)-3-(2,3-Difluorophenyl)-1-isobutylpyrrolidin-3-OL

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Reaction Steps

Preparation according to Example 38: 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), 1-bromo-2-methylpropane (0.32 mL, 2.97 mmol). Stirred 4 h. Purification by flash chromatography on silica gel (ethyl acetate/methanol, 2:1). Yield: 0.16 g. [α]D=−16.1° (methanol). The amine was converted to the oxalic acid salt and recrystallized from ethanol/diethyl ether: M.p. 176° C.; MS m/z (relative intensity, 70 eV) 255 (M+3), 182 (45), 213 (12), 127 (6) 212 (bp).

Provenance & Evidence