HCID 22141214, compound → HCID 22141191, compound

HRID 1826507Notes

Reaction equation

HRID 1826507 reaction equation
[CH2:1]([CH:7]1[C:12](=[O:13])[CH:11]2[N:9]([C:10]2([CH3:23])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N+:20]([O-])=O)[C:8]1=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]>O1CCCC1.[Pd]>[NH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:10]1([CH3:23])[N:9]2[CH:11]1[C:12](=[O:13])[CH:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[C:8]2=[O:24]

Participants

4

Reactant 1

HCID 22141214HCID 22141214, compound

Product 1

HCID 22141191HCID 22141191, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-hexyl-6-methyl-6-(2-nitrophenyl)azabicyclo[3.1.0]hexane-2,4-dione (Preparation 138, 880 mg, 2.66 mmol) in tetrahydrofuran (10 ml) was added 5% palladium on charcoal (Johnsson Matthey type 87, 50 mg) and the reaction mixture was placed under an atmosphere of hydrogen (60 psi) at room temperature for 4 h. The catalyst was removed by filtration through Celite™ and the filtrate was concentrated in vacuo. The residue was flushed through a small plug of silica gel (<1 g) eluting with dichloromethane to afford only the exo isomer of the title compound as a pale yellow oil (310 mg, 39%).

Workup

  1. customThe catalyst was removed by filtration through Celite™
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was flushed through a small plug of silica gel (<1 g)
  4. washeluting with dichloromethane

Sources & evidence

ORD record
ord-736032e4ccd147779c04026918c251b1
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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