Dimethylformamide → 1-(tert-butyl) 3-methyl 3-(N-methylformamido)pyrrolidine-1,3-dicarboxylate

HRID 1038096Notes

Reaction equation

HRID 1038096 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1([NH:19][CH:20]=[O:21])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]1)=[O:6].[CH3:22]N(C=O)C.CI>C1COCC1>[CH3:3][O:4][C:5]([C:7]1([N:19]([CH:20]=[O:21])[CH3:22])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH2:8]1)=[O:6]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 576860951-(Tert-butyl) 3-methyl 3-formamidopyrrolidine-1,3-dicarboxylate

Product 1

HCID 576862341-(tert-butyl) 3-methyl 3-(N-methylformamido)pyrrolidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in oil) (10 mg, 0.25 mmol) was added to a solution of 3-Formylamino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (2T) (50 mg, 0.183 mmol) in THF (3 ml). DMF (1 ml) was added and stirred for 1 hour. Methyl iodide (0.1 ml, 1.60 mmol) was added and the reaction was stirred overnight. The solvent was evaporated and the residue extracted with EtOAc (50 ml), washed with H2O (20 ml), dried over MgSO4, filtered and solvent evaporated yielding a residue which chromatographed on silica gel eluting with 3% MeOH/MeCl2 yielding 3T (50 mg, 94%). LCMS (MH 287) Retention time=2.77 minutes.

Workup

  1. stirringthe reaction was stirred overnight
  2. customThe solvent was evaporated
  3. extractionthe residue extracted with EtOAc (50 ml)
  4. washwashed with H2O (20 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customsolvent evaporated
  8. customyielding a residue which
  9. customchromatographed on silica gel eluting with 3% MeOH/MeCl2 yielding 3T (50 mg, 94%)

Sources & evidence

ORD record
ord-4a9b17a89f5d4ff58c5313a12f182c1d
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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