Water → tert-butyl (6R,7S)-6-(3,4-dichlorophenyl)-7-ethenyl-1,4-oxazepane-4-carboxylate

Temperature

-78 °C

A suspension of methyltriphenylphosphonium bromide (3.59 g) in THF (30 mL) was cooled under nitrogen purging to −78° C., and 1.6 M n-butyllithium/hexane solution (5.79 ml) was added. The mixture was warmed to 0° C., and stirred for 20 min, and a solution of tert-butyl (6R,7R)-6-(3,4-dichlorophenyl)-7-formyl-1,4-oxazepane-4-carboxylate (2.89 g) in THF (50 ml) was added. After stirring at 0° C. for 20 min, and at room temperature for 2 hr, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-30%)) to give the title compound (1.10 g) as a colorless oil.

1. temperatureThe mixture was warmed to 0° C.
2. stirringAfter stirring at 0° C. for 20 min
3. waitat room temperature for 2 hr
4. extractionthe mixture was extracted with ethyl acetate
5. washThe organic layer was washed with brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customthe solvent was evaporated
8. customThe residue was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (0%-30%))

ORD record

ord-aec5be62a44e4c53b535f14fa2feb49f

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722662B2