Cyclopentylamine → (R)-tert-butyl 3-cyano-1-(cyclopentylamino)-1-oxopropan-2-ylcarbamate

Participants

Reaction Steps

To a mixture of (R)-2-(tert-butoxycarbonylamino)-3-cyanopropanoic acid (0.5 g, 2.334 mmol), HATU (0.986 g, 2.59 mmol) and cyclopentanamine (0.461 mL, 4.67 mmol) in DCM (10 mL) was added Et3N (0.651 mL, 4.67 mmol). The reaction mixture was stirred at room temperature for 5 h and then washed with saturated aqueous NaHCO3 and brine. The organics were dried over MgSO4 and concentrated. Purification by silica column chromatography (MeOH/DCM, 0-10%) afforded the title compound (0.61 g, 93%). 1H NMR (400 MHz, CD3OD) δ 1.50 (s, 9 H) 1.57-1.73 (m, 4 H) 1.79-1.87 (m, 3 H) 1.89-2.02 (m, 1 H) 2.05-2.19 (m, 3 H) 2.76-2.95 (m, 1 H) 3.87 (t, J=7.07 Hz, 1 H).

Provenance & Evidence