Sodium borohydride → HCID 68668071, compound

HRID 216391Notes

Reaction equation

HRID 216391 reaction equation
[BH4-].[Na+].[F:3][CH:4]([F:51])[C:5]([C:38]1[CH:43]=[CH:42][C:41]([C:44]2[CH:49]=[CH:48][C:47]([F:50])=[CH:46][N:45]=2)=[CH:40][CH:39]=1)([OH:37])[CH2:6][C:7]1[N:8]([C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:9]=[C:10]([CH2:12][C:13]([CH3:17])([CH3:16])[CH:14]=[O:15])[N:11]=1>CO>[F:51][CH:4]([F:3])[C:5]([C:38]1[CH:39]=[CH:40][C:41]([C:44]2[CH:49]=[CH:48][C:47]([F:50])=[CH:46][N:45]=2)=[CH:42][CH:43]=1)([OH:37])[CH2:6][C:7]1[N:8]([C:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:9]=[C:10]([CH2:12][C:13]([CH3:17])([CH3:16])[CH2:14][OH:15])[N:11]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86638503HCID 86638503, compound

Product 1

HCID 68668071HCID 68668071, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (8 mg, 0.2 mmol) was added to a solution of 3-(2-{3,3-difluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]-2-hydroxypropyl}-1-trityl-1H-imidazol-4-yl)-2,2-dimethylpropanal (70 mg, 0.1 mmol) in methanol (3 mL). After stirring at ambient temperature until the reaction was complete (LCMS), the reaction mixture was quenched with water and extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo to afford 3-(2-{3,3-difluoro-2-[4-(5-fluoropyridin-2-yl)phenyl]-2-hydroxypropyl}-1-trityl-1H-imidazol-4-yl)-2,2-dimethylpropan-1-ol which was used without further purification.

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with methylene chloride
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-87f7a163770c430b86dec282d7f3cd9b
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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