Water → HCID 178520962, compound

HRID 2368157Notes

Reaction equation

HRID 2368157 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]3[C:19]([CH:20]=2)=[N:18][N:17]([C@H:21]2[CH2:26][CH2:25][C@H:24]([C:27](OC)=[O:28])[CH2:23][CH2:22]2)[CH:16]=3)[CH2:9][CH2:8]1.O.[OH-].[Na+]>C1COCC1>[CH:7]1([CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]3[C:19]([CH:20]=2)=[N:18][N:17]([C@H:21]2[CH2:26][CH2:25][C@H:24]([CH2:27][OH:28])[CH2:23][CH2:22]2)[CH:16]=3)[CH2:9][CH2:8]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178501170HCID 178501170, compound

Product 1

HCID 178520962HCID 178520962, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (0.462 g) in THF (100 mL) was added dropwise a solution of methyl trans-4-[6-(cyclopropylmethoxy)-2H-indazol-2-yl]cyclohexanecarboxylate (4.00 g) in THF (100 mL) under ice-cooling. The reaction mixture was stirred under ice-cooling for 2 hr, and water (0.462 mL), 5N aqueous sodium hydroxide solution (0.462 mL) and water (0.462 mL) were carefully added successively thereto. The reaction mixture was stirred under ice-cooling for 30 min, and the resulting precipitate was filtered off. The obtained filtrate was concentrated under reduced pressure to give the title compound (3.51 g).

Workup

  1. temperaturecooling
  2. temperaturecooling for 2 hr
  3. stirringThe reaction mixture was stirred under ice-
  4. temperaturecooling for 30 min
  5. filtrationthe resulting precipitate was filtered off
  6. concentrationThe obtained filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-82fe3ed589984df3925c369fbe271735
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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