Trifluoroacetic acid → HCID 50925149, compound

Temperature

70 °C

To 1-(2,3,4,5-tetrahydrothieno[2,3-f][1,4]oxazepin-8-yl)cyclobutanol (1.00 g) were added triethylsilane (4.90 ml) and trifluoroacetic acid (4.73 ml) in this order under ice-cooling, and the mixture was stirred at 70° C. for 1 hr. The solvent was evaporated under reduced pressure, ice water (10 ml) and 8N aqueous sodium hydroxide solution (10 mL) were added to the residue, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (solvent gradient; 0→50% ethyl acetate/hexane) to give 8-cyclobutyl-2,3,4,5-tetrahydrothieno[2,3-f][1,4]oxazepine as an oil. Ethyl acetate (5 mL) and 4N hydrogen chloride-ethyl acetate solution (5 mL) were added thereto, and the solvent was evaporated under reduced pressure. The residue was recrystallized from a mixed solvent of MeOH and Et2O to give 8-cyclobutyl-2,3,4,5-tetrahydrothieno[2,3-f][1,4]oxazepine 1 hydrochloride (360 mg, 47.7%) as a solid.

1. temperaturecooling
2. customThe solvent was evaporated under reduced pressure, ice water (10 ml) and 8N aqueous sodium hydroxide solution (10 mL)
3. additionwere added to the residue
4. extractionthe mixture was extracted with ethyl acetate
5. dry with materialThe extract was dried over anhydrous magnesium sulfate
6. customthe solvent was evaporated under reduced pressure
7. customthe residue was purified by silica gel column chromatography (solvent gradient; 0→50% ethyl acetate/hexane)

ORD record

ord-9f002b36d89541cbabcde33168f6fae9

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916549B2