3-Cyanopyridine → (R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester

HRID 1026176Notes

Reaction equation

HRID 1026176 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([CH:13]=[CH2:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CC=C(C#N)C=1.[OH:23]O>C[Re](=O)(=O)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([CH:13]2[CH2:14][O:23]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 793-CyanopyridineHCID 784Hydrogen PeroxideHCID 66975072(S)-tert-Butyl 3-vinylpyrrolidine-1-carboxylate

Product 1

HCID 86664072(R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl esterYield 64.8%

Reagents, catalysts & solvents 1

HCID 178477782HCID 178477782, compoundCatalyst

Procedure

To (S)-3-Vinyl-pyrrolidine-1-carboxylic acid t-butyl ester (50 g, 253.4 mmol, 1.0 eq.) was added 3-pyridinecarbonitrile (2.7 g, 25.3 mmol, 0.1 eq.) and methyltrioxorhenium (VII) (1.3 g, 5.1 mmol, 0.02 eq.). The mixture was stirred until homogeneous. 30% Hydrogen peroxide (11.2 g, 329.5 mmol, 1.3 eq.) was added, and the mixture was maintained below 35° C. The mixture was then extracted with EtOAc, washed with water, dried over Na2SO4, and purified by column chromatography (hexanes:EtOAc=1:3, 3 L) to give (R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester (35 g).

Workup

  1. temperaturethe mixture was maintained below 35° C
  2. extractionThe mixture was then extracted with EtOAc
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. custompurified by column chromatography (hexanes:EtOAc=1:3, 3 L)

Sources & evidence

ORD record
ord-0596ae3781ce45449ab675c5a302b8cc
Source dataset
uspto-grants-2014_05
Patent number
US08729119B2

Reaction notes

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