Lithium Hydroxide → HCID 22933861, compound

HRID 1269801Notes

Reaction equation

HRID 1269801 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][CH:11]3[CH2:16][CH2:15][CH:14]([C:17]([O:19]CC)=[O:18])[CH2:13][CH2:12]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[OH-].[Li+]>CO.O1CCCC1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][CH:11]3[CH2:12][CH2:13][CH:14]([C:17]([OH:19])=[O:18])[CH2:15][CH2:16]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 22934049HCID 22934049, compound

Product 1

HCID 22933861HCID 22933861, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The ethyl 4-(1H-indazol-5-yloxy)cyclo-hexanecarboxylate (728.4 mg, 2.53 mmol) obtained in Example 367 was dissolved in a mixture of methanol (2.5 ml) and tetrahydrofuran (2.5 ml), and a 2M-aqueous lithium hydroxide solution (2.53 ml, 5.05 mmol) was added dropwise thereto. After 2 hours, the reaction mixture was concentrated under reduced pressure and the resulting residue was dissolved in water (5 ml). The resulting aqueous solution was adjusted to pH 4 with a 0.5M-aqueous potassium hydrogensulfate solution. The crystals formed were filtered under reduced pressure and then dried to obtain 4-(1H-indazol-5-yloxy)cyclohexanecarboxylic acid (381 mg, 58%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe resulting residue was dissolved in water (5 ml)
  3. customThe crystals formed
  4. filtrationwere filtered under reduced pressure
  5. customdried

Sources & evidence

ORD record
ord-b630d4a84dc642d2b34cee7f48e5d07f
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

Loading…