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

To a stirred solution of 3-hexyl-6-(3-nitrophenyl)-6-propyl-3-azabicyclo[3.1.0]hexane-2,4-dione (Preparation 64, 0.28 g, 0.78 mmol) in tetrahydrofuran (3 ml), under nitrogen, was added borane tetrahydrofuran complex (1M in tetrahydrofuran, 1.7 ml, 1.7 mmol) and the reaction mixture was heated under reflux for 2 h. The reaction mixture was cooled to room temperature, methanol (1.5 ml) was added and then the reaction mixture was heated under reflux for 16 h. The reaction mixture was concentrated in vacuo and the residue was dissolved in methanol (14 ml) and refluxed for 5 h. The reaction mixture was concentrated in vacuo, methanol (14 ml) was added and the reaction mixture was refluxed for a further 3 h before concentrating in vacuo. The crude residue was purified by chromatography on a Biotage Flash12M™ cartridge packed with silica gel (8 g), eluting with hexane:ethyl acetate (4:1) to give the title compound as a yellow oil (0.2 g, 79%).

1. temperaturethe reaction mixture was heated
2. temperatureunder reflux for 2 h
3. temperaturethe reaction mixture was heated
4. temperatureunder reflux for 16 h
5. concentrationThe reaction mixture was concentrated in vacuo
6. dissolutionthe residue was dissolved in methanol (14 ml)
7. temperaturerefluxed for 5 h
8. concentrationThe reaction mixture was concentrated in vacuo, methanol (14 ml)
9. additionwas added
10. temperaturethe reaction mixture was refluxed for a further 3 h
11. concentrationbefore concentrating in vacuo
12. customThe crude residue was purified by chromatography on a Biotage Flash12M™ cartridge
13. washeluting with hexane:ethyl acetate (4:1)

ORD record

ord-fea95b7be3784e2f9e4890f1776d3584

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06313312B1