HCID 86586672, compound → HCID 86586671, compound

HRID 2088144Notes

Reaction equation

HRID 2088144 reaction equation
C([N:8]1[C@@H:13]2[C@H:14]([CH2:16][OH:17])[CH2:15][C@@:9]1([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C@H:10]([O:18][CH2:19][C:20]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:21]=1)[CH2:11][CH2:12]2)C1C=CC=CC=1>[Pd]>[F:28][C:26]([F:27])([F:29])[C:24]1[CH:25]=[C:20]([CH2:19][O:18][C@@H:10]2[CH2:11][CH2:12][C@@H:13]3[NH:8][C@@:9]2([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:15][C@H:14]3[CH2:16][OH:17])[CH:21]=[C:22]([C:30]([F:31])([F:32])[F:33])[CH:23]=1

Participants

3

Reactant 1

HCID 86586672HCID 86586672, compound

Product 1

HCID 86586671HCID 86586671, 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-hydroxymethyl-1-phenyl-8-azabicyclo[3.2.1]octane (Example 28; 85 mg 0.15 mmol), 10% palladium on charcoal (125 mg, 0.12 mmol) ethanol (10 ml) was stirred under hydrogen atmosphere (1 atm) at +65° C. 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 ethylacetate: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-d23fb4792cab49da96df666601c1cf34
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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