Ammonium cerium (IV) nitrate → 5,6,7,8-tetrahydro-2-(phenoxymethyl)-4H-thiazolo[5,4-c]azepin-4-one

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Reaction Steps

A solution of ammonium cerium (IV) nitrate (1.08 g, 1.97 mmol) in H2O (1.5 mL) was added to a stirred solution of 5,6,7,8-tetrahydro-5-[(4-methoxyphenyl)methyl]-2-(phenoxymethyl)-4H-thiazolo[5,4-c]azepin-4-one (0.22 g, 0.56 mmol) in ACN (5 mL). The mixture was stirred at room temperature for 16 hours and then diluted with H2O and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 100/0). The desired fractions were collected and the solvents evaporated in vacuo to yield 5,6,7,8-tetrahydro-2-(phenoxymethyl)-4H-thiazolo[5,4-c]azepin-4-one (0.081 g, 52%) as a white solid. C14H14N2O2S LCMS: Rt 1.59, m/z 275 [M+H]+ (using method, LC-MS Method 6).

Provenance & Evidence