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

HRID 2353131Notes

Reaction equation

HRID 2353131 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:17]#[N:18])([CH3:16])[CH3:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=[O:20].[K+].[K+].OO.O>CS(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]([C:17](=[O:20])[NH2:18])([CH3:16])[CH3:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 57420353tert-Butyl 4-(2-cyanopropan-2-yl)piperazine-1-carboxylate

Product 1

HCID 574203541,1-Dimethylethyl 4-(2-amino-1,1-dimethyl-2-oxoethyl)-1-piperazinecarboxylateYield 309.7%

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 tert-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-77f123cb716047f094b17779fdaadabf
Source dataset
uspto-grants-2010_07
Patent number
US07750002B2

Reaction notes

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