HCID 86586642, compound → HCID 86586654, compound

HRID 2088132Notes

Reaction equation

HRID 2088132 reaction equation
C([N:8]1[C@@H:13]2[C@H:14]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:15][C@@:9]1([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C@@H:10]([O:25][CH2:26][C:27]1[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:28]=1)[CH:11]=[CH:12]2)C1C=CC=CC=1>[Pd].C(O)C>[F:36][C:33]([F:34])([F:35])[C:31]1[CH:32]=[C:27]([CH2:26][O:25][C@H:10]2[CH2:11][CH2:12][C@@H:13]3[NH:8][C@@:9]2([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH2:15][C@H:14]3[S:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)(=[O:18])=[O:17])[CH:28]=[C:29]([C:37]([F:40])([F:38])[F:39])[CH:30]=1

Participants

4

Reactant 1

HCID 86586642HCID 86586642, compound

Product 1

HCID 86586654HCID 86586654, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (1R*,2S*,5S*,6R*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]oct-3-ene (Description 6; 390 g, 0.59mol), 10% palladium on charcoal (473 mg) and ethanol (25 ml) was stirred under hydrogen atmosphere (1 atm) at +70° C. for 2 hours and at room temperature overnight. The reaction mixture was cooled to room temperature, flushed with nitrogen gas and filtered through a pad of Celite™. The filtrate was concentrated and purified by flash chromatography to give the title compound (250 mg, 74%). The hydrochloride salt of the title compound was prepared by treatment with ethereal HCl and recrystallized from dichloromethane-ether.

Workup

  1. customat room temperature
  2. customovernight
  3. customflushed with nitrogen gas
  4. filtrationfiltered through a pad of Celite™
  5. concentrationThe filtrate was concentrated
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-8fc3152ee8e742ad84f2385b73931d79
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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