Lithium Hydroxide → 1-[(tert-butoxy)carbonyl]-1H,2H,3H-pyrrolo[2,3-b]pyridine-2-carboxylic acid

HRID 2220499Notes

Reaction equation

HRID 2220499 reaction equation
CC[O:3][C:4]([CH:6]1[N:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH2:7]1)=[O:5].[OH-].[Li+]>C1COCC1.CO.O>[C:18]([O:17][C:15]([N:14]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH2:7][CH:6]1[C:4]([OH:5])=[O:3])=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 691087141-tert-butyl 2-ethyl 2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-1,2-dicarboxylate

Product 1

HCID 691091501-[(tert-butoxy)carbonyl]-1H,2H,3H-pyrrolo[2,3-b]pyridine-2-carboxylic acidYield 44.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 2,3-dihydro-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (1 g) and lithium hydroxide (0.25 g) in 6 ml THF, 3 ml MeOH and 3 ml water was stirred 0.5 h at rt. The reaction mixture was poured onto 1M HCl/ice and washed three times with dichloromethane. The aqueous layer was neutralized with 1M NaOH, evaporated to dryness and purified by chromatography (silica gel, dichloromethane/methanol, 4/1) to yield 2,3-dihydro-pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid 1-tert-butyl ester as a white solid (400 mg). MS: 263.4 (M−H)−

Workup

  1. washwashed three times with dichloromethane
  2. customevaporated to dryness
  3. custompurified by chromatography (silica gel, dichloromethane/methanol, 4/1)

Sources & evidence

ORD record
ord-3e5098bb215443dea62fce0a3c9f689c
Source dataset
uspto-grants-2008_08
Patent number
US07417144B2

Reaction notes

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