反应详情

To a stirred mixture of p-iodothiophenol (1.75 g, 7.43 mmol) and N-(tert-butoxycarbonyl)-2-pyrrolidinylmethyl p-toluenesulfonate (2.39 g, 6.75 mmol) in pyridine (12.7 mL) was added 8N KOH (1.27 mL) at room temp, and the resulting mixture was stirred for 4 hr at the same temp. The reaction mixture was diluted with EtOAc. The solution was washed with H2O, sat NH4Cl, brine, and dried over Na2SO4. The organic layer was concentrated under a reduced pressure. The residue was chromatographed on silica-gel with n-hexane-EtOAc (5:1, v/v) as eluent to afford 1.49 g (53%) [N-(tert-butoxycarbonyl)-2-pyrrolidinyl]methyl 4-iodophenyl sulfide as a pale yellowish oil. 1H-NMR (400 MHz, CDCl3) δ(s, 9H), 1.78-2.01(br m, 4H), 2.71 (dt, 1H), 3.32-3.49 (br m, 3H), 3.90-4.02 (br m, 1H), 7.12 (d, J=7.8 Hz, 1H), 7.18 (d, J=7.8 Hz, 1), 7.57 (dd, J=2.0, 8.3 Hz, 2H); MS (FAB) m/z 420(M++1).

1. washThe solution was washed with H2O
2. dry with materialdried over Na2SO4
3. concentrationThe organic layer was concentrated under a reduced pressure
4. customThe residue was chromatographed on silica-gel with n-hexane-EtOAc (5:1