ethyl (1R,3R,4S)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate → ethyl (1S,3R,4R)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate

HRID 347806Notes

Reaction equation

HRID 347806 reaction equation
[C:1]1([C@@H:7]([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)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(OCC)(=O)C.[Pd]>[C:1]1([C@@H:7]([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[CH2:11][CH2:12]3)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 10730826ethyl (1R,3R,4S)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

Product 1

HCID 11054856ethyl (1S,3R,4R)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylateYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl (1R, 3R, 4S)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate (791 mg, 2.91 mmol) obtained in Example 3 (a) in ethyl acetate (15 ml) was added 10% Pd—C (53 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 16 hours. After a filtration through Celite, the solvent was concentrated. The residue was purified by silica gel column chromatography (5% ethyl acetate/hexane), to give ethyl (1S, 3R, 4R)-2-[(S)-1-phenylethyl]-2-azabicyclo[2.2.1]heptane-3-carboxylate (601 mg, 76%).

Workup

  1. filtrationAfter a filtration through Celite
  2. concentrationthe solvent was concentrated
  3. customThe residue was purified by silica gel column chromatography (5% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-566a90f6671149cc9a456c721a1522a3
Source dataset
uspto-grants-2007_02
Patent number
US07176217B2

Reaction notes

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