Potassium Hydroxide → (S)-2-((S)-1-azido-2-phenylethyl)oxirane

HRID 440112Notes

Reaction equation

HRID 440112 reaction equation
[OH-].[K+].[N:3]([C@@H:6]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C@H:7]([OH:20])[CH2:8]OS(C1C=CC(C)=CC=1)(=O)=O)=[N+:4]=[N-:5]>C(O)C>[N:3]([C@H:6]([C@H:7]1[CH2:8][O:20]1)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[N+:4]=[N-:5]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 117602043(S)-azido-4-phenyl-1-(p-toluenesulphonyloxy)-2(S)-butanol

Product 1

HCID 10954320(S)-2-((S)-1-azido-2-phenylethyl)oxiraneYield 65.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 280 mg (5 mmol) of potassium hydroxide in 10 ml of ethanol were added to a solution of 1.37 g (3.8 mmol) of 3(S)-azido-4-phenyl-1-(p-toluenesulphonyloxy)-2(S)-butanol in 50 ml of ethanol and the mixture was stirred at room temperature for 1 hour. The mixture was then evaporated to dryness and the residue was partitioned between water and dichloromethane. The aqueous phase was back-extracted twice with dichloromethane. The organic phases were combined, dried over anhydrous magnesium sulphate and evaporated to give an oil which was purified by flash chromatography on silica gel using n-hexane/ethyl acetate (4:1) for the elution. There was obtained 0.47 g of 2(S)-[1(S)-azido-2-phenylethyl]oxirane: MS: m/e 189 [M]+.

Workup

  1. customThe mixture was then evaporated to dryness
  2. customthe residue was partitioned between water and dichloromethane
  3. extractionThe aqueous phase was back-extracted twice with dichloromethane
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated
  6. customto give an oil which
  7. customwas purified by flash chromatography on silica gel
  8. washfor the elution

Sources & evidence

ORD record
ord-5788c50bceb445d7bf4df605ce49ccc5
Source dataset
uspto-grants-1996_05
Patent number
US05516913

Reaction notes

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