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a
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6
reaction mixture was stirred at room temperature for 30 min. On
completion of the reaction as indicated by TLC, the mixture was
quenched with water and extracted with ethyl acetate. The organic layer
was washed with brine and dried over Na2SO4. The solvent was evaporated
in vacuo, and the crude product was chromatographed on silica gel (EtOAc–
hexane mixture) to afford pure diastereoisomers in good yield.
Representative spectral data of the products: Compound 7d: yellow colored
liquid; IR (KBr) 3398.3 (NH), 1339.5, 1156.2 cmÀ1 1H NMR (400 MHz,
;
CDCl3) d 1.15 (s, 3H), 1.24 (s, 3H), 2.16 (dt, Ha, J = 8.0, 10.8 Hz), 2.43 (s, 3H),
2.73 (dd, 1H, J = 8.0,10.8 Hz), 3.31 (dd, 1H J = 10.8, 4.0 Hz), 3.46–3.48 (m,
1H, Hb, J = 4.0, 10.8 Hz), 3.85(t, 1H, J = 4.0 Hz), 4.12 (br s, NH), 6.79–7.63
(Ar-7H); 13C NMR (400 MHz, CDCl3)
d 21.50, 26.97, 32.54, 33.27, 48.71,
49.02, 50.91, 56.49, 114.34, 121.47, 125.54, 126.60, 127.33, 129.09, 129.67,
134.00, 138.99, 143.36; MS (m/z) 390.19 (M+); Anal. Calcd for
C20H23N2O2SCl; C, 61.45, H, 5.93, N, 7.17. Found: C, 61.33, H, 6.07, N,
7.05.Compound 8d: yellow colored liquid; IR (KBr) 3379.1 (NH), 1339.5,
1160.1 cmÀ1 1H NMR (400 MHz, CDCl3) d 1.07 (s, 3H), 1.25 (s, 3H), 1.92 (dt,
;
Ha, J = 8.0,12.0 Hz), 2.41 (s, 3H), 3.00 (t, 1H, J = 12.0 Hz), 3.21 (dd, 1H,
J = 12.0, 12.0 Hz), 3.28 (distorted dt, Hb, J = 12.0, 12.0 Hz), 3.55 (dd, 1H,
J = 8.0, 8.0 Hz), 3.81(dd, 1H, J = 12, 8.0 Hz), 4.12 (br s, NH), 6.40–7.74 (Ar-
7H); 13C NMR (400 MHz, CDCl3) d 21.52, 26.74, 28.55, 34.62, 46.87, 50.09,
50.62, 53.18, 116.97, 123.54, 126.62, 126.97, 127.29, 132.80, 134.07, 141.68,
143.71; MS (m/z) 390.52 (M+); Anal. Calcd For C20H23N2O2SCl; C, 61.45, H,
5.93, N, 7.17. Found: C, 61.36, H, 5.83, N, 7.26.
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