Methanol → 3-Hexyl-6-isopropyl-6-(3-nitrophenyl)-3-azabicyclo[3.1.0]hexane

To a stirred solution of 3-hexyl-6-isopropyl-6-(3-nitrophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione (Preparation 59, 0.57 g, 1.6 mmol) in tetrahydrofuran (6 ml), under nitrogen, was added borane tetrahydrofuran complex (1M in tetrahydrofuran, 3.0 ml, 3.0 mmol) and the reaction mixture was heated under reflux for 2 h. The reaction mixture was cooled to room temperature before the addition of further borane tetrahydrofuran complex (1M in tetrahydrofuiran, 3.0 ml, 3.0 mmol). After 20 min, the reaction mixture was cooled to room temperature and methanol (8 ml) was added and then the reaction mixture was once more heated under reflux for 6 h. The reaction mixture was concentrated in vacuo and the residue was dried under vacuum at room temperature. The residue was treated with dichloromethane (4 ml), filtered and purified by chromatography on a Biotage Flash40S™ cartridge packed with silica gel (40 g) eluting with hexane:ethyl acetate (6:1). The title compound was obtained initially as a yellow oil which crystallised upon standing (0.2 g, 40%).

1. temperaturethe reaction mixture was heated
2. temperatureunder reflux for 2 h
3. temperaturethe reaction mixture was cooled to room temperature
4. temperaturethe reaction mixture was once more heated
5. temperatureunder reflux for 6 h
6. concentrationThe reaction mixture was concentrated in vacuo
7. customthe residue was dried under vacuum at room temperature
8. additionThe residue was treated with dichloromethane (4 ml)
9. filtrationfiltered
10. custompurified by chromatography on a Biotage Flash40S™ cartridge
11. washeluting with hexane:ethyl acetate (6:1)

ORD record

ord-e2640ac7594a4065a7e8497bfd838899

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313312B1