(1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octan-6-carboxylic acid trifluoroacetate → (1R*,2R*,5S*,6R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octan-6-carboxylic acid trifluoroacetate

HRID 2088193Notes

Reaction equation

HRID 2088193 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].C([N:15]1[C@@H:20]2[C@H:21]([C:23]([OH:25])=[O:24])[CH2:22][C@@:16]1([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C@H:17]([O:26][CH2:27][C:28]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[C:30]([C:38]([F:41])([F:40])[F:39])[CH:29]=1)[CH2:18][CH2:19]2)C1C=CC=CC=1>[Pd].C(O)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[F:41][C:38]([F:39])([F:40])[C:30]1[CH:29]=[C:28]([CH2:27][O:26][C@@H:17]2[CH2:18][CH2:19][C@@H:20]3[NH:15][C@@:16]2([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:22][C@H:21]3[C:23]([OH:25])=[O:24])[CH:33]=[C:32]([C:34]([F:36])([F:37])[F:35])[CH:31]=1

Participants

4

Reactant 1

HCID 86586685(1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octan-6-carboxylic acid trifluoroacetate

Product 1

HCID 86586738(1R*,2R*,5S*,6R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octan-6-carboxylic acid trifluoroacetateYield 110.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (1R*,2R*,5S*,6R*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octan-6-carboxylic acid trifluoroacetate (Example 53; 2.7 g, 4 mmol), 10% palladium on charcoal (500 mg) and ethanol (30 ml) was stirred under hydrogen atmosphere (1 atm) at +40° C. for 20 minutes. The reaction mixture was cooled to room temperature, flushed with nitrogen gas and filtered through a pad of Celite™. The filtrate was concentrated to give the title compound (2.6 g) as a white solid.

Workup

  1. customflushed with nitrogen gas
  2. filtrationfiltered through a pad of Celite™
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9ea7d8f181084dd89de669aabb71e5ea
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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