Lithium Hydroxide → 3-(((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid

HRID 1968186Notes

Reaction equation

HRID 1968186 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][CH2:15][C:16]2[C:24]3[C:23]([C:25]([O:27]C)=[O:26])=[CH:22][CH:21]=[N:20][C:19]=3[N:18](C(OC(C)(C)C)=O)[CH:17]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][CH2:15][C:16]2[C:24]3[C:23]([C:25]([OH:27])=[O:26])=[CH:22][CH:21]=[N:20][C:19]=3[NH:18][CH:17]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67225102HCID 67225102, compound

Product 1

HCID 672231593-(((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-tert-butyl 4-methyl 3-(((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate (70 mg, 0.143 mmol) in dioxane (2 mL) was added 1N LiOH (0.358 mL, 0.358 mmol) at 0° C. and stirred for 4 h at rt. The reaction mixture was extracted with ether and the aqueous layer was neutralized with 1N HCl, and concentrated in vacuo to afford 3-(((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid as an off-white solid. [M+H] found 375.

Workup

  1. extractionThe reaction mixture was extracted with ether
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-874ba7aa161948d6b27b9661754f5b8d
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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