Benzyl succinimido carbonate → 1-benzyl 4-(tert-butyl) (S)-2-methylpiperazine-1,4-dicarboxylate

HRID 1970545Notes

Reaction equation

HRID 1970545 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][C@@H:10]([CH3:14])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:15]([O:22][C:23](ON1C(=O)CCC1=O)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])(O)=O.[Na+]>O1CCOCC1.O.C(OCC)(=O)C>[C:4]([O:3][C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:23]([O:22][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:24])[C@@H:10]([CH3:14])[CH2:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 83172Benzyl succinimido carbonateHCID 516892Sodium BicarbonateHCID 7023035(S)-1-Boc-3-methylpiperazine

Product 1

HCID 299217161-benzyl 4-(tert-butyl) (S)-2-methylpiperazine-1,4-dicarboxylate

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of 2.5 g (S)-4-N-Boc-2-methyl-piperazine, 3.5 g N-(Benzyloxycarbonyl-oxy)succinimide and 2.0 g NaHCO3 in 10 ml dioxane/water 1/1 was stirred for 12 h. The mixture was diluted with ethyl acetate, the phases separated and the organic phase washed with water, saturated aqueous NaHCO3, 0.1 M HCl and brine. The crude product obtained after drying over MgSO4 and evaporation of the solvents was used in the subsequent reaction. Yield: 4.3 g.

Workup

  1. customthe phases separated
  2. washthe organic phase washed with water, saturated aqueous NaHCO3, 0.1 M HCl and brine

Sources & evidence

ORD record
ord-b50f3e54159c4796beb239df86159881
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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