Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 87485026, compound

HRID 884115Notes

Reaction equation

HRID 884115 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[CH3:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1)=O.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>C1(C)C=CC=CC=1>[F:30][C:29]([F:31])([F:32])[C:26]1[CH:25]=[CH:24][C:23]([C:21](=[N:1][C:2]2[CH:3]=[CH:4][C:5]([O:8][C:9]3[CH:19]=[CH:18][C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:10]=3)=[N:6][CH:7]=2)[CH3:20])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 697311-(4-(Trifluoromethyl)phenyl)ethan-1-oneHCID 68523649HCID 68523649, compound

Product 1

HCID 87485026HCID 87485026, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl 4-(5-aminopyridin-2-yloxy)benzoate (16.0 g, 62 mmol) was dissolved in toluene (300 mL). To the resulting solution were added 4-trifluoromethylacetophenone (11.7 g, 62 mmol) and (±)-camphor-10-sulfonic acid (1.08 g, 4.65 mmol), and refluxed overnight. The reaction solution was concentrated under reduced pressure, to thereby yield 26.5 g of the title compound.

Workup

  1. temperaturerefluxed overnight
  2. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-6ff067b986e642a5b9314a977f20076f
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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