Water → HCID 22933367, compound

HRID 1269803Notes

Reaction equation

HRID 1269803 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH:17]3[CH2:22][CH2:21][CH:20]([C:23](OCC)=[O:24])[CH2:19][CH2:18]3)=[CH:13][CH:14]=2)[CH:9]=[N:8]1.O.[OH-].[Na+]>O1CCCC1>[NH:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH:17]3[CH2:18][CH2:19][CH:20]([CH2:23][OH:24])[CH2:21][CH2:22]3)=[CH:13][CH:14]=2)[CH:9]=[N:8]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 22934049HCID 22934049, compound

Product 1

HCID 22933367HCID 22933367, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (52 mg, 1.39 mmol) was added to a solution of the ethyl 4-(1H-indazol-5-yloxy)cyclohexanecarboxylate (100 mg, 0.347 mmol) obtained in Example 367 in tetrahydrofuran (2 ml), and the resulting mixture was refluxed. After 2 hours, water (52 μl), a 2M-aqueous sodium hydroxide solution (0.104 ml) and then water (0.156 ml) were added to the reaction mixture, and the resulting solution was filtered by the use of Celite. The filtrate was concentrated under reduced pressure, and the resulting oil was crystallized by the addition of diisopropyl ether. The crystals were filtered under reduced pressure and then dried to obtain [4-(1H-indazol-5-yloxy)cyclohexyl]methanol (72 mg, 84%, trans/cis=4/1).

Workup

  1. temperaturethe resulting mixture was refluxed
  2. filtrationthe resulting solution was filtered by the use of Celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe resulting oil was crystallized by the addition of diisopropyl ether
  5. filtrationThe crystals were filtered under reduced pressure
  6. customdried

Sources & evidence

ORD record
ord-de34b1d3bff04062b1c2244cc48f1f06
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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