Methyl iodide → HCID 66864982, compound

HRID 2093108Notes

Reaction equation

HRID 2093108 reaction equation
[NH:1]1[C:5]2[CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9][C:4]=2[CH:3]=[C:2]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].[H-].[Na+].[CH3:24]I>C1COCC1>[CH3:24][N:1]1[C:5]2[CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9][C:4]=2[CH:3]=[C:2]1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66864693HCID 66864693, compound

Product 1

HCID 66864982HCID 66864982, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-tert-butyl 2-ethyl 1,4,5,7-tetrahydro-6H-pyrrolo[2,3-c]pyridine-2,6-dicarboxylate (1.0 eq) in dry THF was added NaH (1.2 eq) at 0° C. and reaction mixture was stirred at room temperature for 30 min. Methyl iodide (6.0 eq.) was added and stirred further at room temperature for 3 hrs. Reaction mixture was quenched with water and extracted with dichloromethane, over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the desired 6-tert-butyl 2-ethyl 1-methyl-1,4,5,7-tetrahydro-6H-pyrrolo[2,3-c]pyridine-2,6-dicarboxylate.

Workup

  1. customreaction mixture
  2. stirringstirred further at room temperature for 3 hrs
  3. customReaction mixture
  4. customwas quenched with water
  5. extractionextracted with dichloromethane, over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto afford crude product, which
  8. customon purification by column chromatography

Sources & evidence

ORD record
ord-983ce2575b0246c38db78299272ae35c
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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