1-Benzyl 4-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate → 1-tert-Butyl 3-methyl piperazine-1,3-dicarboxylate

HRID 1260462Notes

Reaction equation

HRID 1260462 reaction equation
[N:1]1(C(OCC2C=CC=CC=2)=O)[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3][CH:2]1[C:14]([O:16][CH3:17])=[O:15]>CO.[Pd]>[N:4]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:5][CH2:6][NH:1][CH:2]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1

Participants

4

Reactant 1

HCID 44519651-Benzyl 4-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate

Product 1

HCID 27568191-tert-Butyl 3-methyl piperazine-1,3-dicarboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd—C (0.2 eq) was added to a stirred RT 0.1 M solution of A2 in MeOH and the mixture was stirred under an H2 atmosphere at RT for 3 h. The mixture was filtered, washing with MeOH, and the filtrate was evaporated under reduced pressure to give the title compound in 95% yield. 1H NMR (400 MHz, CDCl3, 300K) δ 4.02 (1H, m), 3.74 (3H, s), 3.70 (1H, m), 3.43 (1H, m), 3.20 (1H, m), 3.04 (2H, m), 2.75 (1H, m), 2.14 (1H, m), 1.47 (9H, s). MS (ES+) C11H20N2O4 requires 244, found: 267 (M+Na)+.

Workup

  1. filtrationThe mixture was filtered
  2. washwashing with MeOH
  3. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d22578413f144f28910634ce36db48ac
Source dataset
uspto-grants-2013_06
Patent number
US08470823B2

Reaction notes

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