3,4-dihydro-2H-pyran → Tert-butyl 4-(2-(tetrahydro-2h-pyran-2-yloxy)ethyl)thiazol-2-ylcarbamate

Participants

Reaction Steps

To a solution of Example 89B (6.3 g, 27.4 mmol) in dichloromethane (100 mL) were added commercially available 3,4-dihydro-2H-pyran (Aldrich) (21 g, 250 mmol) and pyridinium-p-toluenesulfonic acid (Aldrich) (3.5 g, 14.0 mmol). The reaction mixture was stirred for overnight at room temperature and then diluted with dichloromethane, washed with water, dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography (SiO2, 0-100% ethyl acetate in hexanes) to afford 7.4 g (82%) of the title compound. MS (ESI+) m/z 329 (M+H)+

Provenance & Evidence