4-Methylbenzylamine → HCID 9455491, compound

Participants

Reaction Steps

To a solution of (S)-1-(tert-butoxycarbonyl)piperidine-3-carboxylic acid (Beta Pharma Inc., 500 mg, 2.181 mmol) and TEA (0.912 mL, 6.54 mmol) in DCM (11 mL) was added HATU (912 mg, 2.399 mmol) followed by 4-methylbenzylamine (0.305 mL, 2.399 mmol). The resulting solution was stirred at room temperature for 48 hours. The reaction was concentrated, and the residue was adsorbed onto a plug of silica gel and purified by chromatography through a 50 g silica gel column, eluting with 0.5% to 5% MeOH in DCM, to provide M5.1 in 70% yield as a white foam. 1H NMR (300 MHz, CDCl3) δ ppm 7.08-7.20 (m, 4H), 6.13 (br. s., 1H), 4.38 (d, J=5.26 Hz, 2H), 3.92 (d, J=13.30 Hz, 1H), 3.62-3.83 (m, 1H), 3.21 (dd, J=13.01, 9.65 Hz, 1H), 3.00 (dd, J=10.40 Hz, 1H), 2.33 (s, 3H), 2.20-2.30 (m, 1H), 1.80-1.95 (m, 2H), 1.58-1.71 (m, 1H), 1.43-1.52 (m, 1H), 1.42 (s, 9H); ESI-MS M+Na 355.2.

Provenance & Evidence