Potassium Carbonate → HCID 178483648, compound

HRID 967153Notes

Reaction equation

HRID 967153 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:22])[CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][O:18]C(=O)C)[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][C@H:11]1[CH2:12][CH2:13][C@H:14]([CH2:17][OH:18])[CH2:15][CH2:16]1)[CH3:22])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178476334HCID 178476334, compound

Product 1

HCID 178483648HCID 178483648, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 18.7 g (59.7 mmol) of trans-acetic acid 4-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-cyclohexylmethyl ester in 110 ml of methanol was added 41.25 g (298.5 mmol) of potassium carbonate. The reaction mixture was then stirred for 2 hours at room temperature. The excess of potassium carbonate was removed by filtration and the methanol was removed by evaporation under reduced pressure. The crude residue was partitioned between ether, 1N hydrogen chloride solution and water. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure and the residue then chromatographed on silica gel with a 2:1 v/v mixture of hexane and ethylacetate as the eluent giving 13.9 g (86.0%) of pure trans-[2-(4-hydroxymethyl-cyclohexyl)-ethyl]-methyl-carbamic acid tert-butyl ester as colorless viscous oil, MS 272 (MH+).

Workup

  1. customThe excess of potassium carbonate was removed by filtration
  2. customthe methanol was removed by evaporation under reduced pressure
  3. customThe crude residue was partitioned between ether, 1N hydrogen chloride solution and water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue then chromatographed on silica gel with a 2:1 v/v mixture of hexane and ethylacetate as the eluent

Sources & evidence

ORD record
ord-92659661187b4865acf8eb4f6547fac4
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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