HCID 86586772, compound → HCID 86586773, compound

HRID 2088223Notes

Reaction equation

HRID 2088223 reaction equation
C([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:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C@H:10]([O:22][CH2:23][C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=1)[CH2:11][CH2:12]2)C1C=CC=CC=1>[Pd].C(O)C>[F:36][C:34]([F:35])([F:37])[C:26]1[CH:25]=[C:24]([CH2:23][O:22][C@@H:10]2[CH2:11][CH2:12][C@@H:13]3[NH:8][C@@:9]2([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH2:15][C@:14]3([C:17]([O:19][CH2:20][CH3:21])=[O:18])[F:16])[CH:29]=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:27]=1

Participants

4

Reactant 1

HCID 86586772HCID 86586772, compound

Product 1

HCID 86586773HCID 86586773, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ((1R*,2R*,5S*,6S*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-ethoxycarbonyl-6-fluoro-1-phenyl-8-azabicyclo[3.2.1]octane (Example 170; 52 mg, 0.085 mmol), 10% palladium on charcoal (123 mg), ethanol (10 ml) was stirred under hydrogen atmosphere (1 atm) at +65° C. for 40 minutes. The reaction mixture was cooled to room temperature, flushed with nitrogen gas and filtered through a pad of Celite™. The filtrate was concentrated. The residue was purified by chromatography on silica gel (dichloromethane:methanol) to give the title compound (13 mg, 30%). The hydrochloride salt of the title compound was prepared by treatment with ethereal HCl.

Workup

  1. customflushed with nitrogen gas
  2. filtrationfiltered through a pad of Celite™
  3. concentrationThe filtrate was concentrated
  4. customThe residue was purified by chromatography on silica gel (dichloromethane:methanol)

Sources & evidence

ORD record
ord-6ca3c0a1b0c140d6944d24e3669ab5eb
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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