Methyl iodide → 1,4-Di-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate

HRID 592066Notes

Reaction equation

HRID 592066 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]1[C:21]([OH:23])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24]([O-])([O-])=O.[Cs+].[Cs+].CI>C(#N)C>[N:8]1([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH:9]1[C:21]([O:23][CH3:24])=[O:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 112559791,4-Di-Boc-piperazine-2-carboxylic acid

Product 1

HCID 224585731,4-Di-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1,4-bis(tert-butoxycarbonyl)piperazine-2-carboxylic acid (2.5 g, 7.56 mol) in acetonitrile (25 mL) was Cs2CO3 (3.93 g, 12.06 mol) with stirring at RT. After 15 min, MeI (2.34 g, 16.48 mol) was added. The reaction mixture was stirred at rt for 14 h. The reaction was monitored by TLC. When SM was finished, reaction mixture was filtered through celite pad and filtrate was concentrated. Column chromatography of crude material afforded product 1,4-di-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate (29) as white solid (2.35 g, 90%).

Workup

  1. stirringThe reaction mixture was stirred at rt for 14 h
  2. customreaction mixture
  3. filtrationwas filtered through celite pad and filtrate
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-5292509452e84d10aee2ad6969b627be
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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