3708
A. Goswami et al. / Tetrahedron: Asymmetry 11 (2000) 3701–3709
under reduced pressure to obtain 0.25 g of epoxide 12f. This was then transferred into a closed
glass tube with 3 ml of t-butyl amine and heated for 4 h at 100°C. After cooling, the excess
reagent was evaporated under reduced pressure and the residue obtained was purified by a silica
gel chromatography (eluent: 4:1 petroleum ether/ethyl acetate). Yield: 0.19 g of 13f (76%); mp
1
129°C; [h]2D5 −23 (c 1, CH2Cl2) (lit.4a −24); H NMR l: 1.2 (9H, 3CH3, s), 2.48 (2H, CH2NBut),
4.67 (1H, CHOH, dd, J=9 and 3.6 Hz), 4.77 (2H, CꢀCH2ꢀO, s), 5.23 (2H, OꢀCH2ꢀO, s), 6.80
(1H, aromat. 7-H, d, J=8.4 Hz), 7.00 (1H, aromat. 5-H, d, J=1.2 Hz), 7.2 (1H, aromat. 8-H,
dd, J=8.4 and 1.2 Hz). Anal. calcd for C14H21NO3: C, 66.91; H, 8.42; N, 5.57; found: C, 66.85;
H, 8.37; N, 5.50%.
Acknowledgements
We thank the Department of Biotechnology, New Delhi, for the financial support and the
Director of the Regional Research Laboratory, Jorhat, for providing the facilities to carry out
this work. We also thank one of the referees for constructive criticism and suggesting some
references to improve the manuscript.
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