Water → tert-Butyl (2-oxopiperidin-1-yl)carbamate

HRID 546701Notes

Reaction equation

HRID 546701 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].NN[C:9]([NH:11][NH2:12])=[O:10].C([O:16][CH2:17][CH3:18])(=O)C.O.[CH2:20]1[CH2:24]OC[CH2:21]1>>[O:16]=[C:17]1[CH2:18][CH2:24][CH2:20][CH2:21][N:12]1[NH:11][C:9](=[O:10])[O:4][C:2]([CH3:5])([CH3:3])[CH3:1]

Participants

6

Reactant 5

HCID 962WaterHCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 73948CarbohydrazideHCID 23665647Potassium tert-butoxide

Product 1

HCID 17896840tert-Butyl (2-oxopiperidin-1-yl)carbamate

Procedure

Potassium tert-butoxide (850 mg) was added to a solution of the carbazide compound (2.03 g) in THF (30 ml) under ice-cooling. The reaction solution was stirred at the same temperature for 30 minutes and at room temperature for further 1.5 hours. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The organic layer was sequentially washed with water and brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 907 mg of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturecooling
  2. customthe organic layer was separated
  3. washThe organic layer was sequentially washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-8d30b9d2f6ad4f4ea2e7f4da5aca4676
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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