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

HRID 657738Notes

Reaction equation

HRID 657738 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 yield 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-3c30009ce582428ebb5a15d19f5c1f4d
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

Loading…