Ethyl Acetate → HCID 69891696, compound

HRID 2088120Notes

Reaction equation

HRID 2088120 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[C@@H:14]([C:16]#[N:17])[CH2:15][C@@:9]1([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:10](=[O:18])[CH:11]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C>[Pd].ClCCl>[CH2:1]([N:8]1[C@@H:13]2[C@@H:14]([C:16]#[N:17])[CH2:15][C@@:9]1([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:10](=[O:18])[CH2:11][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 69889417HCID 69889417, compound

Product 1

HCID 69891696HCID 69891696, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (1R*,5S*,6S*)-8-benzyl-6-cyano-1-phenyl-8-azabicyclo[3.2.1]oct-3-en-2-one (Description 39b; 44 g, 140 mmol), 10% palladium on charcoal (11 g, 10 mmol), ethyl acetate (200 ml) was stirred under hydrogen atmosphere (1 atm) at room temperature for 1.5 hours. The reaction mixture was treated with dichloromethane (500 ml), filtered through a pad of Celite™. The Celite™ cake was well washed with dichloromethane to dissolve solid product. The filtrate was concentrated to give the title compound.

Workup

  1. filtrationfiltered through a pad of Celite™
  2. washThe Celite™ cake was well washed with dichloromethane
  3. dissolutionto dissolve solid product
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3bcfc8b1e83a4517ae744d4998f90cfb
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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