[OH:1][CH2:2][CH:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(C)C=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[C:10]1([C@@H:9]2[N:7]3[C:6](=[O:8])[CH2:5][CH2:4][CH:3]3[CH2:2][O:1]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1A mixture of 5-hydroxymethyl-2-pyrrolidone (85.0 g), benzaldehyde (98.0 g), p-toluenesulfonic acid (1.6 g) and toluene (500 ml) was heated to reflux using a Dean-Stark water separator and an oil bath, with vigorous stirring. After nine hours, the collection of water stopped and the cooled reaction mixture was washed with 5% sodium bicarbonate solution (2×50 ml), saturated sodium bisulfide solution (4×50 ml), water (2×50 ml) and brine (1×50 ml). The toluene solution was dried over andydrous magnesium sulfate and the solvent removed on a rotary evaporator. The residue obtained was distilled, 145°-150° C./0.1 mm Hg to give the title compound as an oil (129.0 g). [α]D =+269.6° (chloroform; c=1). TLC single spot at Rf =0.5 (silica gel, ethyl acetae-hexane; 4:1 UV and iodine).
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