Lithium borohydride → 2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanol

HRID 216395Notes

Reaction equation

HRID 216395 reaction equation
[BH4-].[Li+].[CH3:3][C:4]([CH3:48])([CH2:46][CH3:47])[CH2:5][C:6]1[N:7]=[C:8]([CH2:30][C:31]([C:33]2[CH:38]=[CH:37][C:36]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][N:40]=3)=[CH:35][CH:34]=2)=[O:32])[N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1>CO>[CH3:3][C:4]([CH3:48])([CH2:46][CH3:47])[CH2:5][C:6]1[N:7]=[C:8]([CH2:30][CH:31]([C:33]2[CH:34]=[CH:35][C:36]([C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][N:40]=3)=[CH:37][CH:38]=2)[OH:32])[N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 686681262-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanone

Product 1

HCID 686683162-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Lithium borohydride (22 mg, 1 mmol) was added to a −78° C. solution of 2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanone (200 mg, 0.33 mmol) in methanol (20 mL). After stirring at ambient temperature for 1.5 h, the reaction mixture was quenched with acetone (1 mL) and concentrated in vacuo. Chromatography over silica eluting with 0-30% ethyl acetate/hexane afforded 2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanol.

Workup

  1. customthe reaction mixture was quenched with acetone (1 mL)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2302f5a4f66e4a9e83926e47e9201c82
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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