HCID 86586680, compound → HCID 86586681, compound

HRID 2088149Notes

Reaction equation

HRID 2088149 reaction equation
C([N:8]1[C@@H:13]2[C@@H:14]([OH: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@@H:14]3[OH:16])[CH:20]=[C:21]([C:29]([F:30])([F:31])[F:32])[CH:22]=1

Participants

3

Reactant 1

HCID 86586680HCID 86586680, compound

Product 1

HCID 86586681HCID 86586681, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of (1R*,2R*,5S*,6S*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octan-6-ol (Example 43; 35 mg 0.065 mmol), 5% palladium on charcoal (150 mg, 0.07 mmol) ethanol (10 ml) was stirred under hydrogen atmosphere (1 atm) at +65° 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 iso-hexane:diethyl ether.

Workup

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

Sources & evidence

ORD record
ord-d403c53002374f4bbb1856fe6c50ef97
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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