Methyl iodide → 4-[Methyl-(2,2,2-trifluoro-acetyl)-amino]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

HRID 1970185Notes

Reaction equation

HRID 1970185 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:7][N:6]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:4].[C:24](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH:8]([N:10]([CH3:24])[C:11](=[O:16])[C:12]([F:15])([F:13])[F:14])[CH2:7][N:6]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 873648974-(2,2,2-Trifluoro-acetylamino)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Product 1

HCID 873659074-[Methyl-(2,2,2-trifluoro-acetyl)-amino]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-(2,2,2-Trifluoro-acetylamino)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (0.26 g, 0.76 mmol) in DMF (2 mL) was added potassium carbonate (0.139 g, 1 mmol) followed by methyl iodide (0.14 g, 1 mmol). The reaction mixture was stirred at 80° C. for 16 hours and partitioned between water and ethyl acetate. The ethyl acetate layer was washed with brine, dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude solid. The crude solid was purified via flash chromatography (50% ethyl acetate in Hexanes) to yield the title compound.

Workup

  1. custompartitioned between water and ethyl acetate
  2. washThe ethyl acetate layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent evaporated in vacuo
  6. customto yield a crude solid
  7. customThe crude solid was purified via flash chromatography (50% ethyl acetate in Hexanes)

Sources & evidence

ORD record
ord-81db8254b4834cd1a604db8ecfa20a77
Source dataset
uspto-grants-2013_04
Patent number
US08426604B2

Reaction notes

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