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

HRID 1826450Notes

Reaction equation

HRID 1826450 reaction equation
[CH2:1]([N:7]1[C:12](=O)[CH:11]2[CH:9]([C:10]2([CH:23]([CH3:25])[CH3:24])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:8]1=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].O1CCCC1.B.CO>O1CCCC1>[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([CH:23]([CH3:24])[CH3:25])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuran2×HCID 221412793-Hexyl-6-isopropyl-6-(3-nitrophenyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

Product 1

HCID 221411753-Hexyl-6-isopropyl-6-(3-nitrophenyl)-3-azabicyclo[3.1.0]hexane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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 tetrahydrofuran, 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%).

Workup

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

Sources & evidence

ORD record
ord-9456ed296e694ea1aec76a3727b7bdf7
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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