Methyl iodide → Tert-butyl 4-methyl-3-oxopiperazine-1-carboxylate

HRID 1922663Notes

Reaction equation

HRID 1922663 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][C:10](=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:17]I>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH3:17])[C:10](=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylate

Product 1

HCID 18783916Tert-butyl 4-methyl-3-oxopiperazine-1-carboxylateYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-oxopiperazine-1-carboxylic acid tert-butyl ester (500 mg, 2.50 mmol) in DMF (20 mL) cooled on an ice-bath was added sodium hydride (120 mg, 3.00 mmol, 60% dispersion in mineral oil) and the resulting mixture stirred for 10 min. Methyl iodide (233 μL, 532 mg, 3.75 mmol) was added and the resulting mixture stirred at room temperature for 18 h. The reaction mixture was quenched with H2O and extracted with EtOAc. The combined organics were dried (Na2SO4) and concentrated in vacuo affording 4-Methyl-3-oxopiperazine-1-carboxylic acid tert-butyl ester as a yellow oil (300 mg, 56%). 1H NMR (CDCl3, 300 MHz): δ 4.08 (s, 2H); 3.65 (t, J=5.4 Hz, 2H); 3.35 (t, J=5.4 Hz, 2H); 3.00 (s, 3H); 1.47 (s, 9H).

Workup

  1. stirringthe resulting mixture stirred at room temperature for 18 h
  2. customThe reaction mixture was quenched with H2O
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e50ddb6228f749e0b38a0cbb90ca7d45
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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