HCID 86586676, compound → HCID 86586675, compound

HRID 2088146Notes

Reaction equation

HRID 2088146 reaction equation
C([N:8]1[C@@H:13]2[C@H:14]([C:16](=[O:21])[N:17]([O:19][CH3:20])[CH3:18])[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]>[F:37][C:34]([F:35])([F:36])[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@H:14]3[C:16](=[O:21])[N:17]([O:19][CH3:20])[CH3:18])[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=1

Participants

3

Reactant 1

HCID 86586676HCID 86586676, compound

Product 1

HCID 86586675HCID 86586675, 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-(N-methoxy-N-methylcarbamoyl)-1-phenyl-8-azabicyclo[3.2.1]octane (Example 37; 420 mg 0.69 mmol), 10% palladium on charcoal (375 mg, 0.35 mmol) ethanol (25 ml) was stirred under hydrogen atmosphere (1 atm) at +60° C. for 1 hour. 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.

Workup

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

Sources & evidence

ORD record
ord-595569e7dcfd437aa37127bd99cca5a1
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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