反应详情

Di-tert-butyl azodicarboxylate (0.1 g, 0.43 mmol) was added to a stirred solution of 6-(4-fluorobenzoyl)-5,6,7,8-tetrahydro-4H-oxazolo[4,5-d]azepine-2-methanol (0.1 g, 0.36 mmol), 4-(tert-butyl-dimethyl-silanyloxy)-phenol (0.097 g, 0.43 mmol) and triphenylphosphine (0.114 g, 0.43 mmol) in THF (0.5 mL) at 0° C. The mixture was stirred at room temperature for 16 hours. Additional di-tert-butyl azodicarboxylate (0.1 g, 0.43 mmol), 4-(tert-butyl-dimethyl-silanyloxy)-phenol (0.097 g, 0.43 mmol) and triphenylphosphine (0.114 g, 0.43 mmol) were added at 0° C. The mixture was stirred at 120° C. for 20 minutes under microwave irradiation. The mixture was diluted with a 1M aqueous solution of NaOH and washed with AcOEt. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 30/70). The desired fractions were collected and the solvents evaporated in vacuo to yield 2-[(4-{[tert-butyl(dimethyl)silyl]oxy}phenoxy)methyl]-5-[(4-fluorophenyl)carbonyl]-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridine (264 mg, 66% purity, 99% yield) as a colorless oil. C26H31FN2O4Si.

1. stirringThe mixture was stirred at 120° C. for 20 minutes under microwave irradiation
2. washwashed with AcOEt
3. customThe organic layer was separated
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. customthe solvents evaporated in vacuo
7. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 30/70)
8. customThe desired fractions were collected
9. customthe solvents evaporated in vacuo