Calcium Chloride → 3-Hexyl-6-(3-aminophenyl)-6-(2,2,2-trifluoroethyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

HRID 428967Notes

Reaction equation

HRID 428967 reaction equation
[CH2:1]([N:7]1[C:12](=[O:13])[CH:11]2[CH:9]([C:10]2([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-])=O)[CH:20]=2)[CH2:14][C:15]([F:18])([F:17])[F:16])[C:8]1=[O:28])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[Cl-].[Ca+2].[Cl-]>C(O)C.O.[Fe]>[CH2:1]([N:7]1[C:8](=[O:28])[CH:9]2[CH:11]([C:10]2([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([NH2:25])[CH:20]=2)[CH2:14][C:15]([F:16])([F:17])[F:18])[C:12]1=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 2

HCID 5284359Calcium ChlorideHCID 221412833-Hexyl-6-(3-nitrophenyl)-6-(2,2,2-trifluoroethyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

Product 1

HCID 221411683-Hexyl-6-(3-aminophenyl)-6-(2,2,2-trifluoroethyl)-3-azabicyclo[3.1.0]hexane-2,4-dioneYield 102.5%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-Hexyl-6-(3-nitrophenyl)-6-(2,2,2-trifluoroethyl)-3-azabicyclo[3.1.0]hexane-2,4-dione (Preparation 103, 178 mg, 0.45 mmol) was dissolved in ethanol (15 ml). Iron powder (225 mg, 4.0 mmol) was added at room temperature followed by calcium chloride (50 mg, 0.45 mmol), dissolved in water (2 ml). The vigorously stirred mixture was heated under reflux for 2 h then cooled to room temperature and filtered through a pad of silica. The solvent was removed in vacuo and the filtrate was dissolved in dichloromethane and filtered through a Whatman anotop 10 plus™ cartridge. The organic mixture was concentrated in vacuo to give the product as a brown gum (170 mg, 100%).

Workup

  1. temperatureThe vigorously stirred mixture was heated
  2. temperatureunder reflux for 2 h
  3. filtrationfiltered through a pad of silica
  4. customThe solvent was removed in vacuo
  5. dissolutionthe filtrate was dissolved in dichloromethane
  6. filtrationfiltered through a Whatman anotop 10 plus™ cartridge
  7. concentrationThe organic mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-b759ef81c710456c983dcd07ee816c82
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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