Methyl iodide → HCID 66864160, compound

HRID 2093095

Reaction equation

HRID 2093095 reaction equation
[NH:1]1[C:9]2[CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5][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:9]2[CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5][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 668643095-Tert-butyl 2-ethyl 6,7-dihydro-1H-pyrrolo[3,2-C]pyridine-2,5(4H)-dicarboxylate

Product 1

HCID 66864160HCID 66864160, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-tert-butyl 2-ethyl 1,4,6,7-tetrahydro-5H-pyrrolo[3,2-c]pyridine-2,5-dicarboxylate (1.0 eq) in THF at 0° C. was added NaH (1.2 eq) and stirred for half an hour at room temperature. Methyl iodide (1.3 eq) was added and resulting reaction mixture was stirred for 3 hrs. Reaction mixture was then quenched with water and extracted with ethyl acetate, dried over sodium sulphate and concentrated to dryness. Crude mass was then purified by silica gel column chromatography to afford 5-tert-butyl 2-ethyl 1-methyl-1,4,6,7-tetrahydro-5H-pyrrolo[3,2-c]pyridine-2,5-dicarboxylate.

Workup

  1. customresulting
  2. customreaction mixture
  3. stirringwas stirred for 3 hrs
  4. customReaction mixture
  5. customwas then quenched with water
  6. extractionextracted with ethyl acetate
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated to dryness
  9. customCrude mass was then purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bd144e7436764823bf42c0c4d1686669
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Linked notes

Loading…