m-Chloroperbenzoic acid → 1,1-Dimethylethyl 4-hydroxy-4-(2-oxiranylmethyl)-1-piperidinecarboxylate

HRID 1059330Notes

Reaction equation

HRID 1059330 reaction equation
[CH2:1]([C:4]1([OH:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:26])C=1.C(=O)([O-])O.[Na+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>ClCCl.C(OCC)(=O)C>[O:26]1[CH2:3][CH:2]1[CH2:1][C:4]1([OH:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 656671Sodium PyrosulfiteHCID 21955339Tert-butyl 4-allyl-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 186702981,1-Dimethylethyl 4-hydroxy-4-(2-oxiranylmethyl)-1-piperidinecarboxylateYield 32.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4.115 g of 4-allyl-1-(tert-butoxycarbonyl)piperidin-4-ol in dichloromethane (100 ml) were added 7.07 g of 3-chloroperbenzoic acid and 2.87 g of sodium hydrogencarbonate and the resulting mixture was heated under reflux for 24 hours. To the reaction mixture were added ethyl acetate and an aqueous solution of sodium metabisulfite and the resulting mixture was stirred for 1 hour. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluted with dichloromethane/ethyl acetate) to thereby give 1.43 g of the title compound as a colorless solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 24 hours
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluted with dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-be803e9f103543d9a4d207806152180e
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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