Aluminium lithium hydride → HCID 178441955, compound

HRID 1971934Notes

Reaction equation

HRID 1971934 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-285ba2f097d446f5876e1a2c6b5d586a
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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