Potassium Carbonate → 2-methoxy-5-[(2R)-oxiran-2-yl]pyridine

HRID 241851Notes

Reaction equation

HRID 241851 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]([OH:22])[C:14]2[CH:15]=[N:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C@@H:13]2[CH2:12][O:22]2)=[CH:15][N:16]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58103580(R)-2-Hydroxy-2-(6-methoxypyridin-3-yl)ethyl 4-methylbenzenesulfonate

Product 1

HCID 581035762-methoxy-5-[(2R)-oxiran-2-yl]pyridineYield 42%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (R)-2-hydroxy-2-(6-methoxypyridin-3-yl)ethyl 4-methylbenzenesulfonate in MeOH (150 mL) at 0° C. was added potassium carbonate (4.4 g, 0.032 mol) and the mixture was stirred at rt overnight. The mixture was filtered through Celite and the filter cake was washed with MeOH. The filtrate was concentrated and the residue was treated with EtOAc (150 mL) and aq. Na2CO3. The organic layer was separated and washed with brine, dried (Na2SO4), and concentrated. The residue was purified by silica gel column to give the desired expoxide as a colorless oil (1.02 g, 42%).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe filter cake was washed with MeOH
  3. concentrationThe filtrate was concentrated
  4. additionthe residue was treated with EtOAc (150 mL) and aq. Na2CO3
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-424dde0314ab4995bf3b160c635725cb
Source dataset
uspto-grants-2014_02
Patent number
US08653091B2

Reaction notes

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