Water → Ethyl 1-[(2S)-2-oxiranylmethyl]-4-piperidinecarboxylate

HRID 1740837Notes

Reaction equation

HRID 1740837 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].[C:12](=[O:15])([O-])[O-].[K+].[K+].O.[C:19](#N)[CH3:20]>>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:19][C@H:20]2[CH2:12][O:15]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 33785968Ethyl 1-[(2S)-2-oxiranylmethyl]-4-piperidinecarboxylate

Procedure

A mixture of 5.7 g (2R)-glycidyl-tosylate (Fluka GmbH), 4 ml piperidine-4-carboxylic acid ethyl ester and 3.5 g potassium carbonate in 100 ml acetonitrile is heated for 2 h under reflux. After cooling the reaction mixture is admixed with 50 ml water and extracted three times each with 50 ml methylene chloride and 50 ml diethyl ether. After drying the combined organic phases over sodium sulfate and removing the solvent on a rotary evaporator, the residue is purified by means of column chromatography on silica gel (ethyl acetate/saturated methanolic ammonia 95/5). In this way 2.5 g (2S)-l-oxiran-2-ylmethyl-piperidine-4-carboxylic acid ethyl ester is obtained.

Workup

  1. temperatureis heated for 2 h
  2. temperatureunder reflux
  3. temperatureAfter cooling the reaction mixture
  4. extractionextracted three times each with 50 ml methylene chloride and 50 ml diethyl ether
  5. dry with materialAfter drying the combined organic phases over sodium sulfate
  6. customremoving the solvent
  7. customon a rotary evaporator
  8. customthe residue is purified by means of column chromatography on silica gel (ethyl acetate/saturated methanolic ammonia 95/5)

Sources & evidence

ORD record
ord-6e5155291acb4976969a3d2d75646c6e
Source dataset
uspto-grants-1999_10
Patent number
US05972947

Reaction notes

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