Methyl 1-benzyl-5-(nitromethylene)-2-pyrrolidinecarboxylate → 8-Benzyl-3,8-diazabicyclo[3.2.1]octan-2-one

HRID 1246702Notes

Reaction equation

HRID 1246702 reaction equation
[CH2:1]([N:8]1[C:12](=[CH:13][N+:14]([O-])=O)[CH2:11][CH2:10][CH:9]1[C:17]([O:19]C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pt].CO>[CH2:1]([N:8]1[CH:12]2[CH2:11][CH2:10][CH:9]1[C:17](=[O:19])[NH:14][CH2:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 66846370Methyl 1-benzyl-5-(nitromethylene)-2-pyrrolidinecarboxylate

Product 1

HCID 219047238-Benzyl-3,8-diazabicyclo[3.2.1]octan-2-one

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

Methyl 1-benzyl-5-(nitromethylene)-2-pyrrolidinecarboxylate (9.92 g, 35.9 mmol) and 5% platinum on activated carbon (11.25 g) were combined in methanol (100 mL) and shaken for 56 hours at ambient temperature under a hydrogen atmosphere (60 psi). The misture was filtered and the filtrate concentrated to provide the title compound. MS (DCI/NH3) m/z: 217 (M+H)+.

Workup

  1. filtrationThe misture was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-b08555579183468dabae223e51a9e25f
Source dataset
uspto-grants-2006_10
Patent number
US07129235B2

Reaction notes

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