Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 56980201, compound

HRID 1977989Notes

Reaction equation

HRID 1977989 reaction equation
[C:1]([CH2:3][C:4]1(O)[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:6][C:5]1([CH3:17])[CH3:16])#[N:2].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH3:15][O:14][C:11]1[CH:12]=[C:13]2[C:8]([CH2:7][CH2:6][C:5]([CH3:17])([CH3:16])[C:4]2=[CH:3][C:1]#[N:2])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 516892Sodium BicarbonateHCID 21996517HCID 21996517, compound

Product 1

HCID 56980201HCID 56980201, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-cyanomethyl-1-hydroxy-7-methoxy-2,2-dimethyl-1,2,3,4-tetrahydronaphthalene (5.27 g, 21.5-mmol) in toluene (50 ml) was added camphor sulfonic acid (0.5 g, 2.15 mmol). The mixture was heated for one hour under reflux. The reaction mixture was poured into a saturated aqueous solution of sodium hydrogencarbonate, and the organic layer was subjected to extraction with chloroform. The extract solution was washed with brine and water, which was dried over magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of a silica gel column chromatography (ethyl acetate:hexane=2:8) to give the above-titled compound (a mixture of isomers) (4.88 g, quantitative).

Workup

  1. temperatureThe mixture was heated for one hour
  2. temperatureunder reflux
  3. extractionthe organic layer was subjected to extraction with chloroform
  4. washThe extract solution was washed with brine and water, which
  5. dry with materialwas dried over magnesium sulfate
  6. distillationby distilling off the solvent under reduced pressure
  7. customThe residue was purified by means of a silica gel column chromatography (ethyl acetate:hexane=2:8)

Sources & evidence

ORD record
ord-20eda346dc004ec0aad733c51a0ccb3d
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

Loading…