Water → 4-Hydroxymethylbicyclo[2.2.2]octane-1-carboxylic acid benzyl ester

HRID 2105694Notes

Reaction equation

HRID 2105694 reaction equation
[CH3:1][O:2][C:3]([C:5]12[CH2:12][CH2:11][C:8]([C:13]3NC4C(=O)N(CCC)C(=O)N(CCC)C=4N=3)([CH2:9][CH2:10]1)[CH2:7][CH2:6]2)=[O:4].C(=O)([O-])[O-].[K+].[K+].C(Br)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[OH2:44]>CN(C=O)C.C(OCC)(=O)C.CCCCCC>[CH2:1]([O:2][C:3]([C:5]12[CH2:6][CH2:7][C:8]([CH2:13][OH:44])([CH2:9][CH2:10]1)[CH2:11][CH2:12]2)=[O:4])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 9844060HCID 9844060, compound

Product 1

HCID 865917484-Hydroxymethylbicyclo[2.2.2]octane-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

4-Hydroxymethylbicyclo[2.2.2]octane-1-carboxylic acid (XVII, Example 14, 24.8 g 135 mmol) is dissolved in DMF (950 ml). Anhydrous potassium carbonate (25 g, 181 mmol) is added to the solution slowly. Benzyl bromide (22 g, 12.94 mmol) is then added. The reaction mixture is heated at 800 for 16 hr. To the reaction mixture is added water (150 ml) and concentrated to give an oil, which was dissolved in ethyl acetate/hexane (5/1, 500 ml). The mixture is washed with saline (2×200 ml), dried over anhydrous sodium sulfate and concentrated to give the title compound, NMR (400 MHz, CDCl3) δ 7.39, 5.11, 3.28, 1.84 and 1.41.

Workup

  1. temperatureThe reaction mixture is heated at 800 for 16 hr
  2. concentrationconcentrated
  3. customto give an oil, which
  4. washThe mixture is washed with saline (2×200 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-68f90d4797464acea32804c2a33f8b28
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

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