Hydrochloric Acid → HCID 86755496, compound

Participants

Reaction Steps

A solution of (2S*,3S*,4R*,5R*)-3-[N-(5-isopropyl-2-methoxybenzyl)amino]-4-methoxycarbonyl-5-methyl-2-phenylpyrrolidine (0.39 g, 0.98 mmol) in 6M HCl aq. solution (6.0 ml) was stirred and heated at a gentle reflux for 30 minutes, wherein precipitation of white solids initiated ca. 10 minutes after refluxing. The reaction mixture was cooled to room temperature, and then EtOH (4.0 ml) was added. After the mixture was ice-cooled for 30 minutes, the white precipitates were filtered off, washed with EtOH (×2), and dried in vacuo at a temperature between 40 and 50 C. for 2 days to afford title compound (0.43 g, 96%) as white needles. ##STR7## mp 159-164 C.: IRmax (nujol): 3400(s), 3200(s), 3130(s), 2370(s), 2300(br., s), 1735(s), 1710(s), 1585(s), 1510(s), 1260(s), 1143(s), 1017(s), 830(s), 770(s), 745(s), 702(s) cm-1 ; 1H-NMR δ (DMSO-d6): 7.907.73(m, 2H), 7.60-7.45(m, 3H), 7.25-7.13(m, 2H), 6.90(d, J=9.2 Hz, 1H), 5.35-5.15(m, 1H), 4.63-4,41(m, 1H), 4.20-4.01(m, 1H), 4.00-3.83(m, 1H), 3.803.15(m, 1H), 3.67(s, 3H), 2.79(sep, J=6.8 Hz, 1H), 2.55-2.42(m, 1H), 1.71(br.d, J=5.9 Hz, 3H), 1.15(d, J=6.8 Hz, 6H) ppm.

Provenance & Evidence