Example 6
Trimethyl aluminum (2M in toluene, 0.38 mmol) was added to a solution of benzyl amine (0.37 mmol) in anhydrous DCM (1 mL) at RT and the resulting mixture was stirred for 15 min. A solution of (S)-tert-butyl 4-(3-(furan-2-carboxamido)-4-methoxy-4-oxobutyl)piperazine-1-carboxylate 30 (0.12 mmol) in anhydrous DCM was added at RT for 3.5 h then NaOH (aq) (1M, 1 mL). The product was extracted with DCM and purification by Biotage™ Isolera (EtOAc in hexane) to obtain the desired product 32 (64%). 1H NMR (CDCl3) δ 8.64 (d, J=6.53 Hz, 1H), 7.46 (d, J=1.00 Hz, 1H), 7.22-7.40 (m, 6H), 7.12 (d, J=3.51 Hz, 1H), 6.52 (dd, J=1.76, 3.51 Hz, 1H), 4.65-4.74 (m, 1H), 4.47-4.56 (m, 1H), 4.38-4.46 (m, 1H), 3.38 (br. s., 4H), 2.56-2.67 (m, 1H), 2.33-2.51 (m, 3H), 2.14-2.31 (m, 3H), 1.91 (ddt, J=3.73, 7.40, 14.74 Hz, 1H), 1.47 (s, 9H).