HCID 22391924, compound → Ethyl 2-azabicyclo[2.2.1]heptane-3-carboxylate

HRID 347797Notes

Reaction equation

HRID 347797 reaction equation
C1(C([N:9]2[CH:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:13]3[CH2:20][CH:10]2[CH:11]=[CH:12]3)C)C=CC=CC=1>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[CH:10]12[CH2:20][CH:13]([CH2:12][CH2:11]1)[CH:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:9]2

Participants

4

Reactant 1

HCID 22391924HCID 22391924, compound

Product 1

HCID 13258847Ethyl 2-azabicyclo[2.2.1]heptane-3-carboxylateYield 22.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of ethyl 2-(1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate (1.29 g, 4.77 mmol) in ethyl acetate (10 ml) was added 20 wt % Pd(OH)2 (1.47 g), and the mixture was stirred under a hydrogen atmosphere at 45° C. for 24 hours. After a filtration through Celite, the solvent was evaporated. The residue was purified by silica gel column chromatography (1%–3% methanol/chloroform), to give ethyl 2-azabicyclo[2.2.1]heptane-3-carboxylate (0.181 g, 22%).

Workup

  1. filtrationAfter a filtration through Celite
  2. customthe solvent was evaporated
  3. customThe residue was purified by silica gel column chromatography (1%–3% methanol/chloroform)

Sources & evidence

ORD record
ord-4f33ab0863c34138aab52e56bab942d9
Source dataset
uspto-grants-2007_02
Patent number
US07176217B2

Reaction notes

Loading…