Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → 1263375-44-5

HRID 1963942Notes

Reaction equation

HRID 1963942 reaction equation
[CH3:1][C:2]([OH:10])([CH3:9])[CH2:3][O:4][CH2:5][CH:6]1[CH2:8][O:7]1.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][C:2]1([CH3:9])[O:10][CH:6]([CH2:8][OH:7])[CH2:5][O:4][CH2:3]1

Participants

5

Reactant 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 516892Sodium BicarbonateHCID 86650637HCID 86650637, compound

Product 1

HCID 669371811263375-44-5Yield 64.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-methyl-1-(oxiran-2-ylmethoxy)propan-2-ol (620 mg, 4.24 mmol) and 10-CSA (300 mg, 1.29 mmol) were dissolved in DCM (30 mL) and stirred at ambient temperature for 24 hr. Saturated NaHCO3 solution was added and the two layers were separated. The aqueous phase was extracted four times with DCM. The organic layers were combined, dried over Na2SO4 and concentrated. The resulting residue was purified on a silica gel column (heptane:EtOAc 1:0 to 1:2) to give the desired product as a colorless oil (400 mg, 64%>). Some starting material was recovered. 1H NMR (400 MHz, CDCl3) δ ppm 3.90-3.96 (1H, m), 3.76 (1H, dd, J= 11.2, 2.8 Hz), 3.56 (1H, dd, J= 11.6, 4.0 Hz), 3.46-3.50 (2H, m), 3.29 (1H, t, J= 11.2 Hz), 3.24 (1H, dd, J= 11.6, 1.2 Hz), 2.69 (1H, br s), 1.35 (3H, s), 1.13 (3H, s).

Workup

  1. customthe two layers were separated
  2. extractionThe aqueous phase was extracted four times with DCM
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting residue was purified on a silica gel column (heptane:EtOAc 1:0 to 1:2)

Sources & evidence

ORD record
ord-0315e60c1da141729a4cfd8fd3b7c15c
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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