1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-pyrazole-3,5-dicarboxylic acid 3-ethyl ester → 2-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-hydroxymethyl-2H-pyrazole-3-carboxylic acid

HRID 604436Notes

Reaction equation

HRID 604436 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[N:8]([CH2:14][C:15]2[CH:19]=[C:18]([C:20]3[S:21][C:22]([Cl:25])=[CH:23][CH:24]=3)[O:17][N:16]=2)[N:7]=1)=O)C>C1COCC1>[Cl:25][C:22]1[S:21][C:20]([C:18]2[O:17][N:16]=[C:15]([CH2:14][N:8]3[C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:6]([CH2:4][OH:3])=[N:7]3)[CH:19]=2)=[CH:24][CH:23]=1

Participants

3

Reactant 1

HCID 602079611-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-pyrazole-3,5-dicarboxylic acid 3-ethyl ester

Product 1

HCID 602079642-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-hydroxymethyl-2H-pyrazole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1 g 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-pyrazole-3,5-dicarboxylic acid 3-ethyl ester in 15 ml THF 314 mg LiBH4 were added cautiously. Then the reaction mixture was stirred for 16 h, quenched with diluted HCl and filtered through a Chem Elut® cartridge by elution with ethyl acetate and DCM. After concentration under reduced pressure the crude residue was directly subjected to the next reaction step.

Workup

  1. customquenched with diluted HCl
  2. filtrationfiltered through a Chem Elut® cartridge by elution with ethyl acetate and DCM
  3. concentrationAfter concentration under reduced pressure the crude residue
  4. customwas directly subjected to the next reaction step

Sources & evidence

ORD record
ord-185cead84ae2421a93e6863b3aee0cba
Source dataset
uspto-grants-2011_03
Patent number
US07910606B2

Reaction notes

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