Trifluoroacetic acid → 4-(Cyclopropylmethoxy)piperidine

Participants

Reaction Steps

A reaction flask was charged with 4-cyclopropylmethoxypiperidine-1-carboxylic acid t-butyl ester (6.80 g, 26.6 mmol) in DCM (15 mL). TFA (7 mL) was added and the reaction was stirred at rt for 4 h. The reaction mixture was quenched with 1 M NaOH and the product extracted into diethyl ether. The combined organic phases were dried over Na2SO4, filtered, and concentrated to give the title compound (3.949 g, 95%). 1H NMR (CD3CD) δ 3.34-3.24 (m, 1H), 3.15 (d, 2H), 2.88-2.82 (m, 2H), 2.44-2.37 (m, 2H), 1.78-1.70 (m, 2H), 1.31-1.21 (m, 2H), 0.89-0.79 (m, 1H), 0.37-0.32 (m, 2H), 0.04-0.00 (m, 2H); 13C NMR (CD3OD) δ 76.2, 73.6, 44.7, 33.2, 11.7, 3.5.

Provenance & Evidence