Aluminium lithium hydride → HCID 178441955, compound

HRID 401928Notes

Reaction equation

HRID 401928 reaction equation
C([O:5][C:6](=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([O:14][C:15]2[N:16]=[N:17][C:18]([CH2:34][CH2:35][CH2:36][CH3:37])=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)=[CH:23][CH:22]=3)[CH:20]=2)[CH2:10][CH2:9]1)(C)(C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:34]([C:18]1[N:17]=[N:16][C:15]([O:14][C@H:11]2[CH2:10][CH2:9][C@H:8]([NH:7][CH:6]=[O:5])[CH2:13][CH2:12]2)=[CH:20][C:19]=1[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:23][CH:22]=1)[CH2:35][CH2:36][CH3:37]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178441956HCID 178441956, compound

Product 1

HCID 178441955HCID 178441955, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of trans-{4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-cyclohexyl}-carbamic acid tert-butyl ester (1 mmol) in anhydrous THF at 0° C. may be treated with LAH in THF (1 M, 2 mL). The reaction may be allowed to come to room temperature. The reaction may be quenched with water and extracted with ethyl acetate. The product may be isolated by flash chromatography using ethyl acetate/hexanes mixtures to give trans-N-{4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-cyclohexyl}-formamide.

Workup

  1. customThe reaction
  2. customto come to room temperature
  3. customThe reaction
  4. custommay be quenched with water
  5. extractionextracted with ethyl acetate
  6. customThe product may be isolated by flash chromatography

Sources & evidence

ORD record
ord-ad22acdf00de4faba4144ab5b309deba
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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