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 251B (6.3 g, 27.4 mmol) in CH2Cl2 (100 mL) was 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 overnight at room temperature and was diluted with CH2Cl2, washed with water, dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography (SiO2, 0-100% ethyl acetate in hexanes) to afford the title compound. MS (ESI+) m/z 329 (M+H)+

Provenance & Evidence