Calcium Chloride → HCID 22141140, compound

HRID 428931Notes

Reaction equation

HRID 428931 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 tetrahydrofuiran, 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 tetrahydrofuiran
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b9a59e2b720a47a9aa66a2ed6ddf2339
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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