HCID 15697757, compound → HCID 11183347, compound

HRID 347800Notes

Reaction equation

HRID 347800 reaction equation
C1([C@H]([N:9]2[C@H:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C@@H:13]3[CH2:20][C@H:10]2[CH:11]=[CH:12]3)C)C=CC=CC=1>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[C@H:10]12[CH2:20][C@H:13]([CH2:12][CH2:11]1)[C@@H:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[NH:9]2

Participants

4

Reactant 1

HCID 15697757HCID 15697757, compound

Product 1

HCID 11183347HCID 11183347, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of ethyl (1S, 3S, 4R)-2-[(R)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate (3.01 g, 11.1 mmol) in ethyl acetate (22 ml) was added 20 wt % Pd(OH)2 (3.89 g) and the mixture was stirred under a hydrogen atmosphere at 45° C. for 60 hours. After a filtration through Celite, the solvent was concentrated. The residue was purified by silica gel column chromatography (1%–2.5% methanol/chloroform), to give ethyl (1R, 3S, 4S)-2-azabicyclo[2.2.1]heptane-3-carboxylate (0.724 g, 39%).

Workup

  1. filtrationAfter a filtration through Celite
  2. concentrationthe solvent was concentrated
  3. customThe residue was purified by silica gel column chromatography (1%–2.5% methanol/chloroform)

Sources & evidence

ORD record
ord-c3dd7650534049959d80c7627320f774
Source dataset
uspto-grants-2007_02
Patent number
US07176217B2

Reaction notes

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