Water → 2,3,4,5-tetrahydrobenzo[b][1,4]oxazepine

Temperature

80 °C

To 1,5-dihydro-4,1-benzoxazepin-2-one (3.7 g, 22.7 mmol) in THF (75 mL) cooled with an ice bath was added lithium aluminum hydride (2.6 g, 68 mmole) portion wise. The reaction mixture was warmed to 80° C. and stirred for 2 hrs. This mixture was then cooled to rt and was treated with water (2.7 mL), 10% sodium hydroxide aqueous solution (2.7 mL) and water (8.1 mL). The resulting mixture was stirred for another 10 minutes before filtration through Celite. The Celite was washed with ethyl acetate and the organic solution was washed with brine (30 mL×2) before drying over MgSO4. Concentration of the filtrate and purification of the residue by silica gel column chromatography eluting with chloroform/methanol (99/1) yielded 1,2,3,5-tetrahydro-4,1-benzoxazepine 2-2 as a brown solid (1.65 g, 48% yield). MS: 150.0 (M+H)+; tR=1.02 min (method 1).

1. temperatureThis mixture was then cooled to rt
2. stirringThe resulting mixture was stirred for another 10 minutes before filtration through Celite
3. washThe Celite was washed with ethyl acetate
4. washthe organic solution was washed with brine (30 mL×2)
5. dry with materialbefore drying over MgSO4
6. customConcentration of the filtrate and purification of the residue by silica gel column chromatography
7. washeluting with chloroform/methanol (99/1)

ORD record

ord-5ee7dbae6ba24cce91f7b972e6681594

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08263588B2