Dimethyl Sulfoxide → Benzyl 4-(oxiran-2-yl)piperidine-1-carboxylate

HRID 1971148Notes

Reaction equation

HRID 1971148 reaction equation
[H-].[Na+].[CH:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1)=[O:4].[CH3:21]S(C)=O>>[O:4]1[CH2:21][CH:3]1[CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[CH2:7][CH2:6]1

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 2776272Benzyl 4-formylpiperidine-1-carboxylate

Product 1

HCID 59305139Benzyl 4-(oxiran-2-yl)piperidine-1-carboxylate

Procedure

To a solution of NaH (10.4 g, 60% dispersion in mineral oil) in DMSO was added (CH3)3SOI (57 g). The reaction mixture was stirred for 30 min at room temperature followed by the dropwise addition at 0° C. of phenylmethyl 4-formyl-1-piperidinecarboxylate (43 g, which can be purchased from AstaTech, Inc., Bristol, Pa.). The mixture was allowed to stir at room temperature for 1 hour and then quenched with water and extracted with Et2O. The organic layer was washed with H2O, brine, dried over MgSO4, filtered and concentrated to yield a white solid.

Workup

  1. stirringto stir at room temperature for 1 hour
  2. customquenched with water
  3. extractionextracted with Et2O
  4. washThe organic layer was washed with H2O, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield a white solid

Sources & evidence

ORD record
ord-307fd5400dbe4b15b2d3ec8b911aed60
Source dataset
uspto-grants-2013_04
Patent number
US08431590B2

Reaction notes

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