Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 70141342, compound

HRID 1597434Notes

Reaction equation

HRID 1597434 reaction equation
[OH:1][C@H:2]([CH2:27][CH2:28][OH:29])[C:3](=[O:26])[CH2:4][S:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[CH:17][CH:16]=2)=[CH:10][CH:9]=1)(=[O:7])=[O:6].[C:30]12(CS(O)(=O)=O)C(C)(C)C(C[CH2:36]1)C[C:31]2=O>CN(C=O)C>[CH3:31][C:30]1([CH3:36])[O:1][C@@H:2]([C:3](=[O:26])[CH2:4][S:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][C:22]([F:23])([F:24])[F:25])=[CH:17][CH:16]=3)=[CH:10][CH:9]=2)(=[O:6])=[O:7])[CH2:27][CH2:28][O:29]1

Participants

4

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 54482327HCID 54482327, compound

Product 1

HCID 70141342HCID 70141342, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Example 270A (1.1 g, 2.4 mmol) and dimethyl acetal (350 mL) in DMF (10 mL) was treated with a catalytic amount of camphorsulfonic acid, stirred at rt for 15 h than partitioned between water ant ethyl acetate. The organics were washed with brine, dried (MgSO4), filtered, concentrated and purified via silca gel column chromatography eluting with 25% hexanes-ethyl acetate to give 693 mg of the title compound as a viscous oil.

Workup

  1. customthan partitioned between water ant ethyl acetate
  2. washThe organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified via silca gel column chromatography
  7. washeluting with 25% hexanes-ethyl acetate

Sources & evidence

ORD record
ord-bde9192f403a4713b7f4dafc86ead53c
Source dataset
uspto-grants-2001_09
Patent number
US06294573B1

Reaction notes

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