Hydrogen Peroxide → 1,1-Dimethylethyl 4-(2-amino-1,1-dimethyl-2-oxoethyl)-1-piperazinecarboxylate

HRID 1689890Notes

Reaction equation

HRID 1689890 reaction equation
[C:1]([C:3]([CH3:14])([CH3:13])[N:4]1[CH2:9][CH2:8][N:7]([C:10]([OH:12])=[O:11])[CH2:6][CH2:5]1)#[N:2].C([O-])([O-])=O.[K+].[K+].OO.[OH2:23]>CS(C)=O>[C:3]([O:11][C:10]([N:7]1[CH2:8][CH2:9][N:4]([C:3]([C:1](=[O:23])[NH2:2])([CH3:14])[CH3:13])[CH2:5][CH2:6]1)=[O:12])([CH3:14])([CH3:13])[CH3:1]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 68899690HCID 68899690, compound

Product 1

HCID 574203541,1-Dimethylethyl 4-(2-amino-1,1-dimethyl-2-oxoethyl)-1-piperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
40 °C

Procedure

To a cooled (ice/water bath) solution of 4-(cyano-dimethyl-methyl)-piperazine-1-carboxylic acid tent-butyl ester (102.9 mg) in dry DMSO was added K2CO3 (9.8 mg) followed by 28% hydrogen peroxide solution (200 μL) dropwise. The resultant was heated at 40° C. overnight. Water was added and the white solid collected, washed with water and air dried to give 4-(1-carbamoyl-1-methyl-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (59.6 mg). (See Tetrahedron 2002, 58, 3217). Treatment of this compound with HCl in DCM/MeOH yielded the desired amine, which was isolated as the hydrochloride salt.

Workup

  1. customthe white solid collected
  2. washwashed with water and air
  3. customdried

Sources & evidence

ORD record
ord-6d1c029a507243ae9d1f2d37a06f867c
Source dataset
uspto-grants-2012_04
Patent number
US08153629B2

Reaction notes

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