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 33262Notes

Reaction equation

HRID 33262 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. Yield: 800 mg.

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-10dda125a7034fc9b1c612e1464b988d
Source dataset
uspto-grants-2008_09
Patent number
US07429581B2

Reaction notes

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