Calcium Chloride → HCID 22141140, compound

HRID 1826441Notes

Reaction equation

HRID 1826441 reaction equation
[CH2:1]([N:4]1[CH2:9][CH:8]2[CH:6]([C:7]2([CH3:19])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=2)[C:5]1=[O:20])[CH:2]=[CH2:3].[Cl-].[Ca+2].[Cl-]>C(O)C.O.[Fe]>[CH2:1]([N:4]1[CH2:9][CH:8]2[CH:6]([C:7]2([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=2)[CH3:19])[C:5]1=[O:20])[CH:2]=[CH2:3]

Participants

6

Reactant 2

HCID 5284359Calcium ChlorideHCID 22141298HCID 22141298, compound

Product 1

HCID 22141140HCID 22141140, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-allyl-6-methyl-6-(3-nitrophenyl)-3-azabicyclo[3.1.0]hexan-2-one (Preparation 50, 10.2 g, 37.5 mmol) in ethanol (850 ml) and water (150 ml) was added iron powder (18.9 g, 337.5 mmol) and calcium chloride (2.1 g, 18.7 mmol). The reaction mixture was refluxed for 5 h, and then filtered to remove the iron powder. The reaction mixture was concentrated in vacuo and the residue was dissolved in dichloromethane:methanol (85:15), filtered and then concentrated in vacuo, dissolved in tetrahydrofuran, filtered and then concentrated in vacuo to give the title compound as a pale yellow foam (9 g, 99%).

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  2. filtrationfiltered
  3. customto remove the iron powder
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. dissolutionthe residue was dissolved in dichloromethane:methanol (85:15)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutiondissolved in tetrahydrofuran
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8dc24819bfc42249e6b6ebe9c691a9c
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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