Carbon Dioxide → 1055880-94-8

Temperature

78 °C

To a solution of tert-butyl 9-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (200 mg, 0.605 mmol) in tetrahydrofuran (4 ml) was added 1.6N solution of n-butyllithium in hexane (0.396 ml, 0.634 mmol) at −78° C., and the mixture was stirred at 78° C. for 1 hr. At −78° C., pulverized dry ice (2 g) was added to the reaction mixture, and the mixture was stirred for 1 hr. Saturated aqueous ammonium chloride solution (5 ml) and 1N hydrochloric acid (5 ml) were added, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate) to give the desired product (40.0 mg, 22.6%) as an oil.

1. customAt −78° C.
2. additionwas added to the reaction mixture
3. stirringthe mixture was stirred for 1 hr
4. extractionthe mixture was extracted with ethyl acetate
5. washThe extract was washed with water
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe solvent was evaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (ethyl acetate)

ORD record

ord-3faaabdc62ce4dc6820cea03a9b54c38

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08247403B2