Triethylamine → (4S)-4-Benzyl-5,5-diphenyl-1,3-oxazolidin-2-one

Participants

Reaction Steps

Trichloromethyl chloroformate (718 mg, 3.63 mmol) was added to a mixture of (S)-2-amino-1,1,3-triphenyl-1-propanol (6) (1.00 g, 3.30 mmol) and triethylamine (710 mg, 7.02 mmol) in CH2Cl2 at 0° C. The reaction mixture was stirred for 5 h at the same temperature and then poured into a brine solution (150 ml). The aqueous layer was made basic with powdered K2CO3 and organics were extracted into dichloromethane (3×50 ml). The combined organic extracts were dried over MgSO4/K2CO3 and concentrated under reduced pressure. The resulting crude product was washed with diethyl ether to obtain the title compound (7) (1.06 g, 97%) as a white solid. m.p. 259–261° C. (lit ? ° C.). [α]D25=−241.94° (c, 0.0211 in DMSO), δH (DMSO-d6) 2.18 (1H, dd, 3J=10.8 Hz, 2J=13.8 Hz, CH2—Ph), 2.52 (1H, dd, 3J=3.6 Hz, 2J=13.8 Hz, CH2—Ph), 4.67 (1H, dd, 3J=3.6 Hz, 3J=10.8 Hz, CH—NH2), 6.90–7.60 (15H, m, Ar—H). δC 44.2 (CH2—Ph), 50.5 (CH—NH), 94.1 (C—O), 130.5, 130.9, 131.5, 132.6, 132.8, 133.0, 133.1, 133.3 and 133.4 (o-, m- and p-Ar), 141.1, 143.4 and 146.5 (α-Ar), 163.7 (C═O), ir 3248 (NH2), 1760 and 1725 (C═O). m/e (CI—NH3) 330 (MH+, 5%), 347 (MNH4+, 6%), 196 (100%).

Provenance & Evidence