Sodium Hydroxide → HCID 58951516, compound

HRID 2421220Notes

Reaction equation

HRID 2421220 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[OH-].[Na+].CC(OC)(C)C.[O:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[O:24][C@H:25]1[CH2:30][CH2:29][CH2:28][C@@H:27]([CH2:31][OH:32])[CH2:26]1>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O>[O:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]1[O:24][C@H:25]1[CH2:30][CH2:29][CH2:28][C@@H:27]([CH2:31][O:32][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH2:26]1

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 79177tert-Butyl bromoacetateHCID 58951520HCID 58951520, compound2×

Product 1

HCID 58951516HCID 58951516, compound

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalystHCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
10 °C

Procedure

34 g of [(1R,3S)-3-(tetrahydropyran-2-yloxy)cyclohexyl]methanol, 100 g of tert-butyl bromoacetate, 16.2 g of tetrabutylammonium bisulfate and 5.9 g of tetrabutylammonium iodide are dissolved in 250 ml of toluene and, at 10° C. (ice-water bath), a solution of 63.5 g of sodium hydroxide in 80 ml of water is added, and the mixture is stirred vigorously (KPG paddle stirrer) at 10° C. for 8 h. Then MTBE and water are added, and the phases are separated. The aqueous phase is extracted twice with MTBE, and the combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel (heptane/ethyl acetate gradient). This results in 36.4 g of tert-butyl [(1R,3S)-3-(tetrahydropyran-2-yloxy)cyclohexylmethoxy]acetate and 6.8 g of [(1R,3S)-3-(tetrahydropyran-2-yloxy)cyclohexyl]methanol as pale yellow oils.

Workup

  1. customthe phases are separated
  2. extractionThe aqueous phase is extracted twice with MTBE
  3. washthe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel (heptane/ethyl acetate gradient)
  7. customThis results in 36.4 g of tert-butyl [(1R,3S)-3-(tetrahydropyran-2-yloxy)cyclohexylmethoxy]acetate

Sources & evidence

ORD record
ord-1b3f2868e12e41a699e98b9c47c54620
Source dataset
uspto-grants-2011_06
Patent number
US07956077B2

Reaction notes

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