Benzyl chloroformate → 1-Benzyl 3-methyl piperazine-1,3-dicarboxylate

HRID 984466Notes

Reaction equation

HRID 984466 reaction equation
[C:1]([CH:5]1[CH2:10][NH:9][CH2:8][CH2:7][NH:6]1)([O:3][CH3:4])=[O:2].Cl[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13]>C([O-])(O)=O.[Na+]>[CH2:15]([O:14][C:12]([N:9]1[CH2:8][CH2:7][NH:6][CH:5]([C:1]([O:3][CH3:4])=[O:2])[CH2:10]1)=[O:13])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 2760426Methyl Piperazine-2-carboxylate

Product 1

HCID 27573841-Benzyl 3-methyl piperazine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

2-Carbomethoxypiperazine was treated with benzyl chloroformate (1.0 eq) in aqueous NaHCO3 to give 1-benzyloxycarbonyl-3-carbomethoxypiperazine. This material was treated with di-tert-butyldicarbonate (1.1 eq) and triethylamine (1.0 eq) in THF to produce 1-tert-butyoxycarbonyl-4-benzyloxycarbonyl-2-carbomethoxypiperazine. Hydrogenation of this compound in methanol using 10% Pd—C gives the title compound after filtration and solvent removal.

Sources & evidence

ORD record
ord-e4636b6319e3412e988d77465204ca2b
Source dataset
uspto-grants-2005_03
Patent number
US06867203B2

Reaction notes

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