Sodium Methoxide → HCID 19809515, compound

HRID 374259Notes

Reaction equation

HRID 374259 reaction equation
Cl.Cl[CH2:3][C:4]1[O:5][C:6]([C:9]23[CH2:16][N:13]([CH2:14][CH2:15]2)[CH2:12][CH2:11][CH2:10]3)=[CH:7][N:8]=1.[CH3:17][O-:18].[Na+]>CO>[CH3:17][O:18][CH2:3][C:4]1[O:5][C:6]([C:9]23[CH2:16][N:13]([CH2:14][CH2:15]2)[CH2:12][CH2:11][CH2:10]3)=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 19809486HCID 19809486, compound

Product 1

HCID 19809515HCID 19809515, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of (±)5-(2-chloromethyl-1,3-oxazol-5-yl)-1-azabicyclo[3.2.1]octane hydrochloride (D25) (75 mg, 0.28 mmole) in dry methanol (2 ml) was added dropwise over 2h to a solution of sodium methoxide in methanol (15 ml of a 25 wt % solution, 66 mmole), under nitrogen, cooled in ice. After evaporation of the solvent in vacuo the residue was treated with saturated aqueous potassium carbonate solution (10 ml) and extracted with chloroform. The combined extracts were dried over sodium sulphate then concentrated in vacuo. The residue was chromatographed on neutral alumina in a gradient of 0-0.5% methanol in chloroform. This afforded the title compound (E11) as an oil (50 mg, 79%) which was converted into the hydrochloride salt m.p. 129°-131° C. (from acetone-ether).

Workup

  1. temperaturecooled in ice
  2. customAfter evaporation of the solvent in vacuo the residue
  3. additionwas treated with saturated aqueous potassium carbonate solution (10 ml)
  4. extractionextracted with chloroform
  5. dry with materialThe combined extracts were dried over sodium sulphate
  6. concentrationthen concentrated in vacuo
  7. customThe residue was chromatographed on neutral alumina in a gradient of 0-0.5% methanol in chloroform

Sources & evidence

ORD record
ord-5fab2c279496486a9f90f8a6db577487
Source dataset
uspto-grants-1992_11
Patent number
US05166357

Reaction notes

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