Water → HCID 22141340, compound

HRID 1826423Notes

Reaction equation

HRID 1826423 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]2[CH:10]([C:11]2([CH3:23])[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-])=O)[CH:15]=2)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[Cl-].[Ca+2].[Cl-]>C(O)C.[Fe]>[NH2:20][C:16]1[CH:15]=[C:14]([C:11]2([CH3:23])[CH:10]3[CH:12]2[CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]3=[O:24])[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 962WaterHCID 5284359Calcium ChlorideHCID 22141218HCID 22141218, compound

Product 1

HCID 22141340HCID 22141340, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-benzyl-6-methyl-6-(3-nitrophenyl)-3-azabicyclo[3.1.0]hexan-2-one (Preparation 28, 2 g, 6.2 mmol) in absolute ethanol (170 ml) was added water (30 ml), calcium chloride (344 mg, 3.1 mmol) and iron powder (3.02 g, 53.8 mmol). The mixture was heated to reflux under nitrogen for 4 h, then cooled. The solution was filtered through silica (10 g) eluting with methanol, then concentrated in vacuo to give the title compound as a white solid (1.73 g, 95%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux under nitrogen for 4 h
  3. temperaturecooled
  4. filtrationThe solution was filtered through silica (10 g)
  5. washeluting with methanol
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a16cdf629704916bc0b480b06a98096
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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