Aluminium lithium hydride → HCID 178441955, compound

HRID 2168656Notes

Reaction equation

HRID 2168656 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-91dab25c7bae49529feb7708aad69629
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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