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

HRID 717592Notes

Reaction equation

HRID 717592 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][C@H:9]1[C:21]([OH:23])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C.C(OCC)(=O)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][C@H:9]1[C:21]([O:23][CH3:24])=[O:22]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 40419050HCID 40419050, compound

Product 1

HCID 573569521,4-Di-tert-butyl 2-methyl (2S)-piperazine-1,2,4-tricarboxylateYield 116.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of solution of (S)-1,4-bis(tert-butoxycarbonyl)piperazine-2-carboxylic acid (18.3 g, 45 mmol) and potassium carbonate (8.2 g; 59 mmol) in DMF (150 ml) cooled to 0° C. under N2, was added dropwise a solution of iodomethane (7.36 ml; 118 mmol). The reaction mixture was left to stir at room temperature for 18 h. It was diluted with ethyl acetate, washed with water and brine. The organic was dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the title compound as a white solid (18 g; 95%). 1H NMR (CDCl3) 1.46-1.50 (18H, d), 1.65 (3H, s), 2.80-2.90 (1H, m), 3.10-3.40 (2H, m), 3.75-4.10 (2H, m), 4.60-4.70 (2H, m).

Workup

  1. waitThe reaction mixture was left
  2. washwashed with water and brine
  3. dry with materialThe organic was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-93d75ad28a134ce0bd23f3559f550dac
Source dataset
uspto-grants-2015_11
Patent number
US09193722B2

Reaction notes

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