HCID 86586674, compound → HCID 86586673, compound

HRID 2088145Notes

Reaction equation

HRID 2088145 reaction equation
C([N:8]1[C@@H:13]2[C@H:14]([C:16]([OH:19])([CH3:18])[CH3:17])[CH2:15][C@@:9]1([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C@H:10]([O:20][CH2:21][C:22]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=1)[CH2:11][CH2:12]2)C1C=CC=CC=1>[Pd]>[F:30][C:28]([F:29])([F:31])[C:26]1[CH:27]=[C:22]([CH2:21][O:20][C@@H:10]2[CH2:11][CH2:12][C@@H:13]3[NH:8][C@@:9]2([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:15][C@H:14]3[C:16]([OH:19])([CH3:18])[CH3:17])[CH:23]=[C:24]([C:32]([F:33])([F:34])[F:35])[CH:25]=1

Participants

3

Reactant 1

HCID 86586674HCID 86586674, compound

Product 1

HCID 86586673HCID 86586673, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of (1R*,2R*,5S*,6R*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(1-hydroxy-1-methylethyl)-1-phenyl-8-azabicyclo[3.2.1]octane (Example 35; 56 mg 0.10 mmol), 10% palladium on charcoal (200 mg, 0.2 mmol) ethanol (10 ml) was stirred under hydrogen atmosphere (1 atm) at +60° C. for 2 hours. 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. The hydrochloride salt of the title compound was prepared by treatment with ethereal HCl and recrystallised from ethyl acetate:iso-hexane.

Workup

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

Sources & evidence

ORD record
ord-5ea2ec10c7fd4e139ab5a521b3b3c061
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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