Water → 3-(Oxan-4-yl)azetidine

Participants

Reaction Steps

To a solution of 3-(tetrahydropyran-4-yl)azetidine-1-carboxylic acid tert-butyl ester (730 mg, 3.0 mmol) in DCM (10 mL) were added water (0.15 mL) and TFA (10 mL). The reaction mixture was stirred at room temperature for 4 hours and the concentrated under reduced pressure to give a residue that was taken up in MeOH. The resulting solution was loaded onto a SCX-2 cartridge (10 g) which was washed with MeOH. The desired product was eluted with a 2M solution of ammonia in MeOH. The appropriate fractions were combined and concentrated to give 3-(Tetrahydropyran-4-yl)azetidine as a yellow oil (393 mg, 92%). 1H NMR (300 MHz, CDCl3): δ 3.96 (dd, J=11.0, 4.0, 2 H); 3.65 (dd, J=8.0, 8.0 Hz, 2 H); 3.44 (dd, J=7.6, 7.6 Hz, 2 H); 3.37 (ddd, J=11.9, 11.9, 2.1, 2 H); 2.50 (m, 1 H); 1.75 (m, 1 H); 1.53 (m, 2 H); 1.18 (ddd, J=25.0, 11.9, 4.3, 2 H).

Provenance & Evidence