Ethyl Acetate → HCID 69891803, compound

HRID 2088118Notes

Reaction equation

HRID 2088118 reaction equation
[CH2:1]([N:8]1[C@@H:13]2[C@@:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])([F:16])[CH2:15][C@@:9]1([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:10](=[O:22])[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@@:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])([F:16])[CH2:15][C@@:9]1([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:10](=[O:22])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 69890358HCID 69890358, compound

Product 1

HCID 69891803HCID 69891803, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (1R*,5S*,6S*)-8-benzyl-6-ethoxycarbonyl-6-fluoro-1-phenyl-8-azabicyclo[3.2.1]oct-3-en-2-one (Description 36; 795 mg, 66 mmol), 10% palladium on charcoal (250 mg), ethyl acetate (5 ml) and ethanol(10 mi) was stirred under hydrogen atmosphere (1 atm) at room temperature for 1 hour. The reaction mixture was treated with dichloromethane (500 ml), filtered through a pad of Celite™. The filtrate was concentrated to give the title compound.

Workup

  1. filtrationfiltered through a pad of Celite™
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-614f4f659f284c37b5a8031878e62aa0
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

Loading…