Toluene → 2,2-dimethylpropionic acid 2-((S)-3-aminopiperidin-1-yl)ethyl ester

Participants

Reaction Steps

To an ice-cooled solution of 2,2-dimethylpropionic acid 2-((S)-3-tert-butoxycarbonylaminopiperidin-1-yl)ethyl ester (2.54 g, 7.73 mmol) in DCM (80 mL) was added TFA (20 mL) and the mixture was stirred at RT for 2 h. Toluene was added and volatiles 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 was eluted with 1M NH3/MeOH. The product containing fractions were combined and concentrated in vacuo affording the title compound as a pale yellow oil (1.567 g, 89%). 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), 2.20-2.12 (1H, m), 2.00-1.94 (1H, m), 1.82-1.65 (2H, m), 1.60-1.46 (1H, m), 1.28 (2H, bs), 1.20 (9H, s), 1.15-1.03 (1H, m).

Provenance & Evidence