Potassium Hydroxide → tert-butyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate

HRID 1437169Notes

Reaction equation

HRID 1437169 reaction equation
C(OC([N:6]1[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[C:8]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)=[CH:7]1)=O)C.[OH-].[K+]>C(O)(C)C>[C:24]([O:23][C:21]([N:18]1[CH2:17][CH2:16][CH:15]([C:8]2[C:9]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:6][CH:7]=2)[CH2:20][CH2:19]1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68896324HCID 68896324, compound

Product 1

HCID 49758876tert-butyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4 g (10.72 mmol) of 3-(1-tert-butoxycarbonyl-piperidin-4-yl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid ethyl ester were added to a solution of 3 g (53.6 mmol) of potassium hydroxide in 120 ml of isopropanol. The mixture was refluxed for 16 hours. The solvent was distilled off and cold water was added. This solution was acidified with concentrated hydrochloric acid and then basified with 8 N aqueous sodium hydroxide solution. This aqueous solution was extracted twice with ethyl acetate. The organic phase was washed with water and brine, dried over magnesium sulphate, filtered and evaporated under reduced pressure. 1.6 g (50% of yield) of the expected product were obtained as yellowish solid.

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. distillationThe solvent was distilled off
  3. additioncold water was added
  4. extractionThis aqueous solution was extracted twice with ethyl acetate
  5. washThe organic phase was washed with water and brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d1c4335b496a4caabfc66b81435985dc
Source dataset
uspto-grants-2009_11
Patent number
US07622480B2

Reaction notes

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