Trifluoroacetic acid → HCID 59605308, compound

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 (1 H, td, J=8.62, 4.35 Hz), 3.84 (1 H, dd, J=8.76, 6.50 Hz), 3.76-3.65 (3 H, m), 3.62 (1 H, dd, J=8.76, 6.50 Hz), 3.38 (2 H, t, J=7.31 Hz), 3.09-3.07 (1 H, m), 2.99-2.88 (1 H, m), 2.64 (1 H, dd, J=12.50, 7.22 Hz), 2.53 (1 H, dd, J=12.50, 7.22 Hz), 2.15 (3 H, s), 2.01 (1 H, dtd, J=12.34, 7.72, 3.21 Hz), 1.83 (1 H, dtd, J=12.35, 8.40, 6.96 Hz)

1. customThe resulting reaction mixture
2. washThe cartridge was washed with DCM/MeOH
3. washthe desired product was subsequently eluted
4. additiona mixture of 2M NH3 in MeOH and DCM

ORD record

ord-b3aced1856e54dc0a33d588c84545eee

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394796B2