Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → (5,5-Dimethyl-1,4-dioxan-2-yl)methanol

HRID 1963946Notes

Reaction equation

HRID 1963946 reaction equation
[CH3:1][C:2]([O:6][CH2:7][CH:8]1[CH2:10][O:9]1)([CH3:5])[CH2:3][OH:4].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O>[CH3:1][C:2]1([CH3:5])[CH2:3][O:4][CH:8]([CH2:10][OH:9])[CH2:7][O:6]1

Participants

6

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 516892Sodium BicarbonateHCID 86650640HCID 86650640, compound

Product 1

HCID 66936837(5,5-Dimethyl-1,4-dioxan-2-yl)methanolYield 86.2%

Reagents, catalysts & solvents 2

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-CatalystHCID 6344DichloromethaneSolvent

Procedure

2-Methyl-2-(oxiran-2-ylmethoxy)propan-1-ol (870 mg, 5.95 mmol) and 10-CSA (207 mg, 15%>) were dissolved in DCM (70 mL) and stirred at ambient temperature for 24 hr. More 10-CSA (100 mg) was added and the solution was stirred overnight. Saturated NaHCO3 solution was added. The two layers were separated and the aqueous layer was extracted twice with DCM. The organic layers were combined, dried over Na2SO4 and concentrated to give the product as a colorless oil (750 mg, 86%). 1H NMR (400 MHz, CDCl3) δ ppm 3.69-3.74 (1H, m), 3.52-3.64 (5H, m), 3.43 (1H, dd, J= 11.6, 0.8 Hz), 2.57 (1H, br s), 1.32 (3H, s), 1.13 (3H, s).

Workup

  1. stirringthe solution was stirred overnight
  2. customThe two layers were separated
  3. extractionthe aqueous layer was extracted twice with DCM
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7d883fff284640ebb95995ddb678997e
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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