(1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(tertbutoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane → (1R*,2R*,5S*,6R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane

HRID 2088141Notes

Reaction equation

HRID 2088141 reaction equation
C([N:8]1[C@@H:13]2[C@H:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@@:9]1([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C@H:10]([O:23][CH2:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([C:35]([F:38])([F:37])[F:36])[CH:26]=1)[CH2:11][CH2:12]2)C1C=CC=CC=1>[Pd]>[F:37][C:35]([F:36])([F:38])[C:27]1[CH:26]=[C:25]([CH2:24][O:23][C@@H:10]2[CH2:11][CH2:12][C@@H:13]3[NH:8][C@@:9]2([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:15][C@H:14]3[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:30]=[C:29]([C:31]([F:32])([F:33])[F:34])[CH:28]=1

Participants

3

Reactant 1

HCID 86586666(1R*,2R*,5S*,6R*)-8-Benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(tertbutoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane

Product 1

HCID 86586665(1R*,2R*,5S*,6R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octaneYield 65,371.898%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of (1R*,2R*,5S*,6R*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane (Example 24; 240 mg, 0.39 mmol), 10% palladium on charcoal (470 mg, 0.40 mmol) ethanol (10 ml) was stirred under hydrogen atmosphere (1 atm) at +65° C. for 1 hour and at room temperature overnight. 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 (iso-hexane:ethyl acetate 0-25%) to give the title compound (135 g, 66%).

Workup

  1. customat room temperature
  2. customovernight
  3. customflushed with nitrogen gas
  4. filtrationfiltered through a pad of Celite™
  5. concentrationThe filtrate was concentrated
  6. customThe residue was purified by chromatography on silica gel (iso-hexane:ethyl acetate 0-25%)

Sources & evidence

ORD record
ord-b3ed6e2758954b7da89d5bf4b2cf6d8b
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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