3,4-dihydro-2H-pyran → Tert-butyl 4-[2-(tetrahydro-2h-pyran-4-yloxy)ethyl]-1,3-thiazol-2-ylcarbamate

Participants

Reaction Steps

To a solution of Example 3B (6.3 g, 27.4 mmol) in dichloromethane (100 mL) were added commercially available 3,4-dihydro-2H-pyran (purchased from Aldrich) (21 g, 250 mmol) and pyridinium-p-toluenesulfonic acid (purchased from Aldrich) (3.5 g, 14.0 mmol). The reaction mixture was stirred overnight at room temperature and then diluted with dichloromethane, washed with water, dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography using an Analogix® IT280™ (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