p-Bromobenzenesulfonyl chloride → 4-Bromo-N-(6,6-dimethylbicyclo[3.1.1]heptan-2-yl)benzene sulfonamide

Participants

Reaction Steps

To a stirred solution of 4-bromo-benzenesulphonyl chloride (0.6 g, 2.34 mmol) in anhydrous CH2Cl2 (5 ml) and Et3N (0.65 ml, excess) at 0° C. was added (−) cis-myrtanylamine (0.36 g, 2.34 mmol) and the stirring was continued overnight at room temperature. The reaction mixture was diluted with CH2Cl2 (15 ml) and washed with H2O (2×100 ml). The organic layer was separated and dried over MgSO4 and the solvent was distilled to afford the title compound (0.87 g, 100%), as pale paste, which was solidified on standing. 1H-NMR (CDCl3) 7.70 (d, 2H, J=6.78 Hz); 6.64 (d, 2H, J=6.90 Hz); 2.91 (t, 2H, J=7.59 Hz); 2.32-2.29 (m, 1H); 2.11-2.06 (m, 1H); 1.91-1.81 (m, 6H); 1.39-1.31 (m, 1H); 1.11 (s, 3H); 0.86 (s, 3H).

Provenance & Evidence