Trifluoroacetic acid → 5-Methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridine

HRID 1396665Notes

Reaction equation

HRID 1396665 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[C:6]2=[CH:7][N:8]=1.FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH2:11][CH2:10][NH:9][C:6]2=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 67133755HCID 67133755, compound

Product 1

HCID 234340355-Methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridineYield 87.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 500 mg of tert-butyl 5-methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridine-1-carboxylate was added 1.5 mL of trifluoroacetic acid, followed by stirring at room temperature for 0.5 hours. The reaction mixture was poured into ice water, neutralized with a 1 M aqueous sodium hydroxide solution, and then chloroform was added to the mixture. The aqueous layer was separated, the organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to obtain 262 mg of 5-methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridine as a pale yellow solid.

Workup

  1. customThe aqueous layer was separated
  2. washthe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d1763ca9ce774a19840c59a72f40da09
Source dataset
uspto-grants-2014_12
Patent number
US08901126B2

Reaction notes

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