HCID 86586679, compound → HCID 86586678, compound

HRID 2088147Notes

Reaction equation

HRID 2088147 reaction equation
C([N:8]1[C@@H:13]2[C:14](=[O:16])[CH2:15][C@@:9]1([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C@H:10]([O:17][CH2:18][C:19]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=1)[CH2:11][CH2:12]2)C1C=CC=CC=1>[Pd]>[F:28][C:25]([F:26])([F:27])[C:23]1[CH:24]=[C:19]([CH2:18][O:17][C@@H:10]2[CH2:11][CH2:12][C@@H:13]3[NH:8][C@@:9]2([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:15][C:14]3=[O:16])[CH:20]=[C:21]([C:29]([F:30])([F:31])[F:32])[CH:22]=1

Participants

3

Reactant 1

HCID 86586679HCID 86586679, compound

Product 1

HCID 86586678HCID 86586678, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of (1R*,2R*,5S*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octan-6-one (Example 41; 53 mg 0.1 mmol), 5% palladium on charcoal (230 mg, 0.11 mmol) ethanol (10 ml) was stirred under hydrogen atmosphere (1 atm) at room temperature for 45 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. The hydrochloride salt of the title compound was prepared by treatment with ethereal HCl and recrystallised from dichloromethane:diethyl ether.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customflushed with nitrogen gas
  3. filtrationfiltered through a pad of Celite™
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e1a7e1fa43f74aa38fad4901e48abeff
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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