HCID 21188455, compound → HCID 15452531, compound

HRID 1953629Notes

Reaction equation

HRID 1953629 reaction equation
[C:1]([N:5]1[CH:9]2[CH2:10][CH2:11][CH:6]1[CH:7]([C:12]1[CH:13]=[CH:14][C:15](Cl)=[N:16][CH:17]=1)[CH2:8]2)([O:3][CH3:4])=[O:2].[H][H]>CO>[C:1]([N:5]1[CH:6]2[CH2:11][CH2:10][CH:9]1[CH2:8][CH:7]2[C:12]1[CH:17]=[N:16][CH:15]=[CH:14][CH:13]=1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 2

HCID 21188455HCID 21188455, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15452531HCID 15452531, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-carbomethoxy-5-(2-chloro-5-pyridyl)-7-aza-bicyclo[2.2.1]hept-2-ene 25 (16 mg) was dissolved in 3 ml methanol containing 7 mg 10% palladium on carbon. The mixture was hydrogenated under a slightly elevated pressure of hydrogen for one hour. After removal of catalyst and solvent, the residue was partitioned between ether and aqueous sodium bicarbonate. The aqueous layer was extracted with ether and the combined organic layer was dried over magnesium sulfate. Removal of solvent gave 10 mg of 7-carbomethoxy-2-(3-pyridyl)-7-azanorbornane (12). MS (CI) m/z 233 (M+1), H1 -NMR 3.72, 3.66 (2s, N-COOCH3).

Workup

  1. customAfter removal of catalyst and solvent
  2. customthe residue was partitioned between ether and aqueous sodium bicarbonate
  3. extractionThe aqueous layer was extracted with ether
  4. dry with materialthe combined organic layer was dried over magnesium sulfate
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-9c6a314c78a74f6cb1387b4cca7b61f6
Source dataset
uspto-grants-2000_09
Patent number
US06117889

Reaction notes

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