Potassium Hydroxide → 5-[(2R)-oxiran-2-yl]-2-(trifluoromethyl)pyridine

HRID 1845121Notes

Reaction equation

HRID 1845121 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]([OH:24])[C:14]2[CH:15]=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=2)(=O)=O)=CC=1.[OH-].[K+]>C1COCC1>[O:24]1[CH2:12][C@H:13]1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:21])([F:22])[F:23])=[N:16][CH:15]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86652106(R)-2-Hydroxy-2-(6-(trifluoromethyl)pyridin-3-yl)ethyl 4-methylbenzenesulfonate

Product 1

HCID 581880495-[(2R)-oxiran-2-yl]-2-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (R)-2-hydroxy-2-(6-(trifluoromethyl)pyridin-3-yl)ethyl 4-methylbenzenesulfonate (1.0 g, 2.77 mmol) in THF (50 mL) was added powder potassium hydroxide (464 mg, 8.28 mmol) in small portions. The mixture was stirred for 40 minutes and TLC indicated completion of the reaction. The mixture was filtered through Celite and the filter cake was washed with acetonitrile (50 mL). The filtrate was carefully concentrated to a half volume and the obtained expoxide solution was used directly for the next step reaction.

Workup

  1. customcompletion of the reaction
  2. filtrationThe mixture was filtered through Celite
  3. washthe filter cake was washed with acetonitrile (50 mL)
  4. concentrationThe filtrate was carefully concentrated to a half volume
  5. customthe obtained expoxide solution was used directly for the next step reaction

Sources & evidence

ORD record
ord-9210e30ce6964e62af517c62aba28e50
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

Loading…