Water → HCID 86330465, compound

HRID 58885Notes

Reaction equation

HRID 58885 reaction equation
[NH:1]1[C:9]2[CH2:8][CH2:7][C@H:6]([C:10]([O:12]C)=[O:11])[CH2:5][C:4]=2[CH:3]=[N:2]1.O.O.[OH-].[Li+]>CO>[NH:1]1[C:9]2[CH2:8][CH2:7][C@H:6]([C:10]([OH:12])=[O:11])[CH2:5][C:4]=2[CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 86317971(S)-methyl 4,5,6,7-tetrahydro-1H-indazole-5-carboxylate

Product 1

HCID 86330465HCID 86330465, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-methyl 4,5,6,7-tetrahydro-1H-indazole-5-carboxylate (500 mg, 2.80 mmol) in methanol (20 mL) were added water (10 mL) and lithium hydroxide hydrate (234 mg, 5.57 mmol) at 0° C. The reaction mixture was stirred at ambient temperature for 2 h and then concentrated to remove most of methanol. The remaining mixture was acidified with diluted aqueous HCl to pH=4 and then concentrated. The residue was dried under vacuum to afford (S)-4,5,6,7-tetrahydro-1H-indazole-5-carboxylic acid (380 mg, 81% yield) as a colorless solid, which was used directly without further purification. (R)-methyl 4,5,6,7-tetrahydro-1H-indazole-5-carboxylate was synthesized in a similar manner.

Workup

  1. concentrationconcentrated
  2. customto remove most of methanol
  3. concentrationconcentrated
  4. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-a91eda8638924bf0b1dce240c3e741de
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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