Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 86751716, compound

HRID 1939708Notes

Reaction equation

HRID 1939708 reaction equation
[CH:1]([C:4]([CH:18]([CH3:20])[CH3:19])([P:14]([OH:17])([OH:16])=[O:15])[O:5][C@@H:6]([CH:12]=[CH2:13])[CH2:7][O:8]COC)([CH3:3])[CH3:2].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>CO>[CH:18]([C:4]([CH:1]([CH3:3])[CH3:2])([P:14]([OH:17])([OH:16])=[O:15])[O:5][C@@H:6]([CH:12]=[CH2:13])[CH2:7][OH:8])([CH3:19])[CH3:20]

Participants

4

Reactant 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 86751717HCID 86751717, compound

Product 1

HCID 86751716HCID 86751716, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-2-O-(Diisopropyl phosphonomethyl)-1-O-methoxymethyl-3-butene-1,2-diol (3.45 g, 11.12 mmol) and camphorsulfonic acid (0.2 g, 0.8 mmol) were mixed in 45 mL of methanol. The resulting solution was heated at reflux for 5 hours. The solvent was evaporated, and the residue was purified by flash chromatography (ethyl acetate:petroleum ether=1:1 to 1:0 then ehtyl acetate:methanol 20:1) to give 2.73 g (92%) of the title compound as an oil.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for 5 hours
  3. customThe solvent was evaporated
  4. customthe residue was purified by flash chromatography (ethyl acetate

Sources & evidence

ORD record
ord-4ac33f7b436a44eead4c3de8f70ec8b4
Source dataset
uspto-grants-1997_12
Patent number
US05696263

Reaction notes

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