Water → Tert-butyl 3-oxo-4-(3-oxopropyl)piperazine-1-carboxylate

HRID 227479Notes

Reaction equation

HRID 227479 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][C:6]1=[O:18])[CH2:2][CH:3]=C.O.I([O-])(=O)(=O)=[O:21].[Na+]>CC(C)=O.[Os](=O)(=O)(=O)=O>[O:18]=[C:6]1[N:5]([CH2:1][CH2:2][CH:3]=[O:21])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7]1

Participants

6

Reactant 3

HCID 962WaterHCID 23667635Sodium periodateHCID 57445033Tert-butyl 4-but-3-enyl-3-oxopiperazine-1-carboxylate

Product 1

HCID 57445034Tert-butyl 3-oxo-4-(3-oxopropyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolvent

Procedure

To a solution of tert-butyl 4-but-3-enyl-3-oxopiperazine-1-carboxylate (0.246 mg, 0.97 mmol) in 10 mL of 1:1 acetone:water was added sodium metaperiodate (621 mg, 2.90 mmol), followed by a solution of 0.25 M aqueous osmium tetraoxide (0.192 mL, 0.048 mmol). After stirring overnight, the reaction was partitioned between EtOAc and brine. The organic phase was dried (Na2SO4), filtered, and concentrated in vacuo to give the titled compound. Proton NMR for the product was consistent with the titled compound. ESI+MS: 257.3 [M+H]+.

Workup

  1. customthe reaction was partitioned between EtOAc and brine
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-24faef6af8424793b89835839fd1d36e
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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