Toluene → 2,2-Dimethylpropionic acid 2-((R)-3-aminopiperidin-1-yl)ethyl ester

Participants

Reaction Steps

To an ice-cooled solution of 2,2-dimethylpropionic acid 2-((R)-3-tert-butoxycarbonylaminopiperidin-1-yl)ethyl ester (2.86 g, 8.72 mmol) in DCM (100 mL) was added TFA (25 mL) and the mixture stirred at RT for 3 h. Toluene was added and volatiles were removed in vacuo. The resulting residue was dissolved in MeOH and loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 1M NH3/MeOH. The product containing fractions were combined and concentrated in vacuo affording the title compound as a colourless oil (1.678 g, 84%). 1H NMR (CDCl3, 300 MHz): 4.18 (2H, t, J=6.0 Hz), 2.89-2.77 (2H, m), 2.68-2.59 & 2.62 (3H, m & t, J=6.0 Hz), 2.19-2.11 (1H, m), 2.00-1.94 (1H, m), 1.84-1.65 (2H, m), 1.60-1.46 (1H, m), 1.23 (2H, bs), 1.20 (9H, s), 1.15-1.03 (1H, m).

Provenance & Evidence