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

HRID 1968190Notes

Reaction equation

HRID 1968190 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([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[NH:18][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[CH2:13][CH2:12][CH2:11][CH:10]([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 67224484HCID 67224484, compound

Product 1

HCID 672243403-((1-(tert-butoxycarbonyl)piperidin-3-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl 3-((1-(tert-butoxycarbonyl)piperidin-3-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylate (315 mg, 0.811 mmol) in dioxane (5 mL) at 0° C. was added 1N LiOH (2.03 mL, 2.03 mmol) and stirred for 4 h at rt. The reaction mixture was partitioned between ether and water. The separated aqueous layer was neutralized with 1N HCl, and concentrated in vacuo to afford 3-((1-(tert-butoxycarbonyl)piperidin-3-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid as an off-white solid. [M+H] found 375.

Workup

  1. customThe reaction mixture was partitioned between ether and water
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34d40b7f955a418e93a72831e9f201ba
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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