Reaction Steps
A 10-mL, two-necked, round-bottomed flask was equipped with a magnetic stirrer, an ice bath, a standard condenser with a N2 inlet, and a glass stopper. To a chilled (5° C.) solution of NaOH pellets (0.1 g, 2.38 mmol) in H2O (1.7 mL) was added a solution of the amine (28, 0.17 g, 1.19 mmol) in CH2Cl2 (1 mL). This was followed by the dropwise addition of a solution of benzoyl chloride (0.2 g, 1.43 mmol) over ~5 min. After stirring for 30 min at 0°-5° C., 30 min at RT, and then 15 min over a steam bath, the mixture was diluted with H2O (15 mL), and the mixture was extracted (CH2Cl2, 3×15 mL). Combining the extracts, drying (Na2SO4, overnight), filtering, and concentrating the solution gave a viscous yellow oil. Chromatography of the oil on alumina (38 g, 2.4 cm×17 cm) employed ethyl acetate as eluant and afforded amide (29) (Rf =0.47) as white crystals (157 mg, 53.3%); mp 95°-96° C. IR (KBr) cm-1 3065, 3045 (Ar C--H), 3000, 2985, 2940, 2910, 2855, 2835 (C--H), 1635 (C=O), 745, 720 (C--H out of plane, mono); 1H NMR (DCCl3) δ1.78-1.93 [m, 3H, H(9) and H(1)], 2.15 [bs, 1H, H(5)], 2.39 [d, 1H, H(4)ax, J=13.9 Hz], 2.77 [d, 1H, H(6)ax, J=12.3 Hz], 3.12-3.21 [m, 3H, H(4)eq and H(6)eq ], 3.41 [d, 1H, H(2)ax, J=12.8 Hz], 3.89 [d, 1H, H(2)eq, J=13.4 Hz), 4.98 [d, 1H, H(8)eq, J=13.1 Hz], 7.38-7.44 [m, 5H, Ar--H]; 13C NMR (DCCl3) ppm 26.53 [C(1)], 26.87 [C(5)], 31.73 [C(2)], 31.78 [C(9)], 32.34 [C(4)], 46.07 [C(8)], 52.12 [C(6)], 126.46, 128.41, 128.83, 137.35 (Ar--C), 170.38 [C=O]. Anal. Calcd. for C14H17NOS: C, 67.98; H, 6.93. Found: C, 68.01; H, 7.07.
