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

HRID 1189473Notes

Reaction equation

HRID 1189473 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 liquid was poured into ice water, and neutralized with a 1 M aqueous sodium hydroxide solution, then chloroform was added thereto, and 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 to obtain 262 mg of 5-methoxy-2,3-dihydro-1H-pyrrolo[2,3-c]pyridine as a pale yellow solid.

Workup

  1. customThe reaction liquid
  2. customthe aqueous layer was separated
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6faf1e6389504736b8dd68a52bfa90f1
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

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