Borane → 2,3,4,5-Tetrahydro-1,5-benzoxazepine

Temperature

70 °C

6,7-Dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one (0.13 g, 0.8 mmol) was dissolved in THF and to this solution was added a 1M solution of borane in THF (1.59 mL, 1.6 mmol). The mixture was heated at 70° C. for 2 hrs. At this time a further portion of borane solution (1.59 mL, 1.6 mmol) was added and heating was continued for another 2 hrs. The solvent was evaporated at this point and the residue was dissolved in ethyl acetate. Extraction of the solution with 1M sodium hydroxide solution and then brine afforded an organic layer that was dried over anhydrous sodium sulfate. The filtrate was evaporated to afford 6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene 2-4 (0.15 g, 100%) that was used without further purification. MS: 150.0 (M+H)+; tR=0.57 min (method 1).

1. temperatureheating
2. customThe solvent was evaporated at this point
3. dissolutionthe residue was dissolved in ethyl acetate
4. extractionExtraction of the solution with 1M sodium hydroxide solution
5. custombrine afforded an organic layer that
6. dry with materialwas dried over anhydrous sodium sulfate
7. customThe filtrate was evaporated

ORD record

ord-a307eeb51e24458888ca86a560959347

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08263588B2