Triethylamine → HCID 59436371, compound

Participants

Reaction Steps

To a solution of (2S,4S)-1-(tert-butoxycarbonyl)-4-hydroxy-2-methylpyrrolidine-2-carboxylic acid (860 mg, 3.51 mmol) and diphenyl phosphorazidate (700 mg, 2.54 mmol) (DPPA) was added Et3N (0.680 mL, 4.88 mmol) at 0° C. The reaction mixture was stirred at RT for 6 h, quenched with water, extracted with EtOAc (3×40 ml). The combined organic layers were washed with water and brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by Biotage (0-30% EtOAc/hex, 1.2 L) to give 101C (235 mg, 49%). 1H NMR (CDCl3, 400 MHz) δ 4.87 (1H, d, J=1.01 Hz), 3.53-3.62 (m, 1H), 3.44-3.53 (m, 1H), 1.98-2.10 (m, 2H), 1.74 (s, 3H), 1.40 (s, 9H); 13C NMR (CDCl3, 101 MHz) δ 172.45 (1C), 154.93 (1C), 81.22 (1C), 75.03 (1C), 64.02 (1C), 53.16 (1C), 46.35 (1C), 28.26 (1C), and 13.96 (3C).

Provenance & Evidence