Methyl morpholine oxide → 6-(4-fluorobenzoyl)-5,6,7,8-tetrahydro-4H-oxazolo[4,5-d]azepine-2-methanol

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Reaction Conditions

Reaction Steps

A 2.5% solution of osmium tetraoxide in tert-BuOH (0.064 mL, 0.005 mmol) was added to a stirred solution of 6-(4-fluorobenzoyl)-5,6,7,8-tetrahydro-2-[(E)-2-phenylethenyl]-4H-oxazolo[4,5-d]azepine (0.037 g, 0.10 mmol) and N-methylmorpholine-N-oxide (0.024 g, 0.20 mmol) in a mixture of THF (0.5 mL) and H2O (0.10 mL). The mixture was stirred at 100° C. for 5 minutes under microwave irradiation. The solvent was evaporated in vacuo and the crude product dissolved in a mixture of MeOH (0.5 mL) and THF (0.5 mL). Then sodium periodate (0.087 g, 0.41 mmol) was added and the mixture stirred at 120° C. for 15 minutes. The mixture was cooled down to 0° C. and sodium borohydride (0.0.15 g, 0.41 mmol) was added portionwise. The mixture was stirred at room temperature for 15 minutes, diluted with a saturated solution of NH4Cl and extracted with AcOEt. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo to yield 6-(4-fluorobenzoyl)-5,6,7,8-tetrahydro-4H-oxazolo[4,5-d]azepine-2-methanol (0.02 g, 67% yield) as a yellow oil that was used in the next step without further purification. C15H15FN2O3 LCMS: Rt 1.74, m/z 291 [M+H]+ (using method, LC-MS Method 2).

Provenance & Evidence