Aluminium lithium hydride → HCID 59644535, compound

HRID 2252010Notes

Reaction equation

HRID 2252010 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[C:9]([C:19]2[N:20]=[N:21][N:22]([CH2:30][C:31]3[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[C:33]([C:41]([F:44])([F:43])[F:42])[CH:32]=3)[C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:8][N:7]=1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:44][C:41]([F:42])([F:43])[C:33]1[CH:32]=[C:31]([CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=1)[CH2:30][N:22]1[C:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:19]([C:9]2[N:10]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[C:6]([CH2:5][CH2:4][OH:3])=[N:7][N:8]=2)[N:20]=[N:21]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86601260HCID 86601260, compound

Product 1

HCID 59644535HCID 59644535, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve [5-[1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazol-4-yl]-4-(2-chloro-benzyl)-4H-[1,2,4]triazol-3-yl]-acetic acid ethyl ester (400 mg) in THF (10 mL). Add LAH (47 mg, soln in 10 mL of THF) at 0° C. and warm to RT overnight. Quench by slowly adding water (0.5 ml), 5N NaOH (0.5 ml) and then more water (3 ml). Filter reaction through Celite® to remove aluminum salts and then purify via radial chromatography using a gradient of 1:1 hexanes:EtOAc to 100% EtOAc to give the title compound (119 mg, 32%). MS (IS) 592.0 (M+1). Rf=0.11 (1:5 hexanes:EtOAc).

Workup

  1. customQuench by slowly adding water (0.5 ml), 5N NaOH (0.5 ml)
  2. filtrationFilter
  3. customreaction through Celite®
  4. customto remove aluminum salts
  5. custompurify via radial chromatography

Sources & evidence

ORD record
ord-180db3aac6914dd0b07b2816a96ecfce
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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