HCID 9961266, compound → HCID 86759432, compound

HRID 2088131Notes

Reaction equation

HRID 2088131 reaction equation
C([N:8]1[CH:13]2[CH: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)[CH: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)[CH2:11][CH2:12]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 9961266HCID 9961266, compound

Product 1

HCID 86759432HCID 86759432, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (1R*,2R*,5S*,6R*)-8S*)-8-benzyl-2-[3,5-bis(trifluoromethyl)-phenylmethoxy]-1-phenyl-6-phenylsulphonyl-8-azabicyclo[3.2.1]octane (Example 1; 450 mg, 0.68 mmol), 5% palladium on charcoal (1 g, 0.47 mmol) and ethanol (20 ml) was stirred under hydrogen atmosphere (1 atm) at +65° C. for 8 hours. 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 (233 mg, 60%). The hydrochloride salt of the title compound was prepared by treatment with ethereal HCl.

Workup

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

Sources & evidence

ORD record
ord-dc3b69d74d5541d586dce8228676e7fe
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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