反应详情

2,2,2-Trifluoroethane-1-thiol (471 μL, 3.41 mmol) was added dropwise to a suspension of sodium hydride (60% dispersion in mineral oil, 0.065 g, 1.636 mmol) in dry DMF (10 mL) at 0 C and the mixture was stirred for 15 min. A solution of tert-butyl 4-[(methanesulfonyloxy)methyl]piperidine-1-carboxylate (prepared in an analogous manner to Intermediate 181, 1 g, 3.41 mmol) in DMF (5 mL) was added dropwise and the mixture was stirred at room temperature for 5 h. The reaction mixture was diluted with water (50 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with saturated aq. sodium bicarbonate (25 mL) then brine (25 mL), dried over magnesium sulfate and concentrated under reduced pressure to provide the title compound as a light yellow oil (1.13 g, quant.). Method B HPLC-MS: MH+ requires m/z=314 Found: m/z=258 (MH+-tBu), Rt=2.39 min (98%).

1. additionwas added dropwise
2. stirringthe mixture was stirred at room temperature for 5 h
3. extractionextracted with EtOAc (3×50 mL)
4. washThe combined organic layers were washed with saturated aq. sodium bicarbonate (25 mL)
5. dry with materialbrine (25 mL), dried over magnesium sulfate
6. concentrationconcentrated under reduced pressure