HCID 86595844, compound → HCID 86595843, compound

HRID 347818Notes

Reaction equation

HRID 347818 reaction equation
[C:1]([C:5]1[C@H:6]2[CH2:11][C@H:9]([CH:10]=1)[N:8]([C@H](C1C=CC=CC=1)C)[C@H:7]2[C:20]([O:22][CH2:23][CH3:24])=[O:21])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[C:1]([CH:5]1[CH2:10][C@@H:9]2[CH2:11][C@@H:6]1[C@H:7]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[NH:8]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86595844HCID 86595844, compound

Product 1

HCID 86595843HCID 86595843, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of ethyl (1R, 3R, 4R)-5-(tert-butyl)-2-[(S)-1-phenylethyl]-2-azabicyclo [2.2.1]hept-5-ene-3-carboxylate (1.22 g, 3.74 mmol) in ethyl acetate (43 ml) was added 20 wt % Pd(OH)2 (0.578 g), and the mixture was stirred under a hydrogen atmosphere at 45° C. for 62 hours. After a filtration through Celite, the solvent was evaporated. The residue was purified by silica gel column chromatography (1%–5% methanol/chloroform), to give ethyl (1R, 3R, 4S)-5-(tert-butyl)-2-azabicyclo[2.2.1]heptane-3-carboxylate (0.197 g, 23%).

Workup

  1. filtrationAfter a filtration through Celite
  2. customthe solvent was evaporated
  3. customThe residue was purified by silica gel column chromatography (1%–5% methanol/chloroform)

Sources & evidence

ORD record
ord-8e09a3dc927b47afb97496c41bd8f64a
Source dataset
uspto-grants-2007_02
Patent number
US07176217B2

Reaction notes

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