3-Bromo-1-propanol → 3-[(2R)-2-Methylpyrrolidin-1-yl]propan-1-ol

Participants

Reaction Steps

3-Bromopropan-1-ol (5.28 mL, 58.4 mmol) was added to a solution of (R)-2-methylpyrrolidine (7.1 g, 58.4 mmol) in water (200 mL). KOH (7.53 g, 134 mmol) was then added and the mixture stirred at ambient temperature for 48 hours. The reaction mixture was then extracted with dichloromethane (5×80 mL) and ethyl acetate (5×80 mL). The combined organic extracts were dried using MgSO4, filtered and concentrated in vacuo. The compound was purified by column chromatography on Biotage® silica gel, eluting with dichloromethane:methanol:ammonia, (90:10:1) to give the title compound as a pale brown oil (5.44, 65%). LCMS (APCI+) 144 (M+H)+.

Provenance & Evidence