Trifluoroacetic acid → HCID 59605308, compound

Participants

Reaction Steps

Trifluoroacetic acid (3 mL) was added to a solution of 3-{[methyl(tetrahydrofuran-3-yl)amino]methyl}azetidine-1-carboxylic acid tert-butyl ester (257 mg, 0.95 mmol) in dichloromethane (12 mL). The resulting reaction mixture was stirred at RT for 1.5 h. The solvents were reduced in vacuo. The resulting residue was loaded onto an Isolute® SCX-2 cartridge (5 g). The cartridge was washed with DCM/MeOH, the desired product was subsequently eluted using a mixture of 2M NH3 in MeOH and DCM to afford (Azetidin-3-ylmethyl)methyl(tetrahydrofuran-3-yl)amine as colourless oil (140 mg, 86%). 1H NMR (400 MHz, CDCl3): δ 3.94 (1H, td, J=8.62, 4.35 Hz), 3.84 (1H, dd, J=8.76, 6.50 Hz), 3.76-3.65 (3H, m), 3.62 (1H, dd, J=8.76, 6.50 Hz), 3.38 (2H, t, J=7.31 Hz), 3.09-3.07 (1H, m), 2.99-2.88 (1H, m), 2.64 (1H, dd, J=12.50, 7.22 Hz), 2.53 (1H, dd, J=12.50, 7.22 Hz), 2.15 (3H, s), 2.01 (1H, dtd, J=12.34, 7.72, 3.21 Hz), 1.83 (1H, dtd, J=12.35, 8.40, 6.96 Hz)

Provenance & Evidence