Lithium hydroxide, monohydrate → HCID 66686823, compound

HRID 1910983Notes

Reaction equation

HRID 1910983 reaction equation
[F:1][CH:2]([F:31])[C:3]1[CH:7]=[C:6]([CH:8]([F:10])[F:9])[N:5]([CH2:11][C:12]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[N:25]=[C:24]([C:26]([O:28]CC)=[O:27])[CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[N:4]=1.O.[OH-].[Li+]>O1CCCC1.O>[F:31][CH:2]([F:1])[C:3]1[CH:7]=[C:6]([CH:8]([F:9])[F:10])[N:5]([CH2:11][C:12]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[N:25]=[C:24]([C:26]([OH:28])=[O:27])[CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[O:13])[N:4]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 66687311HCID 66687311, compound

Product 1

HCID 66686823HCID 66686823, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 6-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)pyridine-2-carboxylate (15.5 g) in tetrahydrofuran (160 ml) and water (40 ml) is added, at room temperature, lithium hydroxide monohydrate (1.99 g). The mixture is stirred at room temperature for 1 hour, and then ice-cold 1N HCl solution is added. The aqueous phase is extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate and concentrated under reduced pressure. This gives 6-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)pyridine-2-carboxylic acid (11.5 g).

Workup

  1. extractionThe aqueous phase is extracted with ethyl acetate
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-594b0b4ad100465c8e02c7a3e047f23b
Source dataset
uspto-grants-2013_12
Patent number
US08604040B2

Reaction notes

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