2-Bromoethanol → 3-(Fluoromethyl)-1-azetidineethanol

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(fluoromethyl)azetidine 2,2,2-trifluoroacetate (Intermediate 6, 100 mg, 0.5 mmol), 2-bromoethanol (60 mg, 0.5 mmol), and potassium carbonate (0.2 g, 1.5 mmol) in acetonitrile (5 mL) was heated to 80° C. overnight. After cooling, solids were filtered off and washed with acetonitrile. The filtrate was concentrated on a rotary evaporator to give a residue that was purified by silica gel chromatography eluting with 10:7 ethyl acetate/hexanes to 10:7:2:1 ethyl acetate/hexane/methanol/triethylamine to afford 52 mg of 2-(3-(fluoromethyl)azetidin-1-yl)ethanol as a pale yellow oil. 1H NMR (DMSO-d6): δ 5.13 (t, 1H), 4.62 (d, 1H), 4.50 (d, 1H), 4.06 (t, 2H), 3.84 (dd, 2H), 3.54 (q, 2H), 3.11 (t, 2H), 3.06-3.03 (m, 1H).

Provenance & Evidence