Water → 6-(3-Aminophenyl)-3-hexyl-6-methyl-3-azabicyclo[3.1.0]hexan-2-one

HRID 428957Notes

Reaction equation

HRID 428957 reaction equation
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([CH3:22])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)[C:8]1=[O:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Cl-].[Ca+2].[Cl-].O>C(O)C.[Fe]>[NH2:19][C:15]1[CH:14]=[C:13]([C:10]2([CH3:22])[CH:9]3[CH:11]2[CH2:12][N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:8]3=[O:23])[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 962WaterHCID 5284359Calcium Chloride2×HCID 221411193-Hexyl-6-methyl-6-(3-nitrophenyl)-3-azabicyclo[3.1.0]hexan-2-one

Product 1

HCID 221411996-(3-Aminophenyl)-3-hexyl-6-methyl-3-azabicyclo[3.1.0]hexan-2-one

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

3-Hexyl-6-methyl-6-(3-nitrophenyl)-3-azabicyclo[3.1.0]hexan-2-one (Preparation 11, 6.3 g, 19.9 mmol) was dissolved in ethanol (250 ml), and iron powder (8.5 g, 0.15 mol), calcium chloride (0.95 g, 8.6 mmol) and water (50 ml) was added. The reaction mixture was refluxed for 2 h. The reaction mixture was cooled to room temperature and calcium chloride (0.95 g, 8.6 mmol) was added, the reaction mixture was refluxed for a further 16 h. The reaction mixture was cooled and filtered and then concentrated in vacuo, the residue was partitioned between dichloromethane and water and the organic layer separated, the aqueous layer was extracted with dichloromethane (3×) and the combined extracts were dried (Na2SO4) and concentrated in vacuo. The title compound was obtained as an orange solid (5.72 g, 100%).

Workup

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. temperaturethe reaction mixture was refluxed for a further 16 h
  3. temperatureThe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customthe residue was partitioned between dichloromethane and water
  7. customthe organic layer separated
  8. extractionthe aqueous layer was extracted with dichloromethane (3×)
  9. dry with materialthe combined extracts were dried (Na2SO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8083f272c3e8459eba116bfeee384e49
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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