Sodium borohydride → HCID 21905518, compound

HRID 1247411Notes

Reaction equation

HRID 1247411 reaction equation
[C:1]([C:3]1[CH:32]=[CH:31][C:6]([CH2:7][NH:8][C:9](=[O:30])[CH:10]([C:14]2[C:19]([F:20])=[CH:18][C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH:27]=[O:28])=[CH:16][C:15]=2[F:29])[O:11][CH2:12][CH3:13])=[CH:5][CH:4]=1)#[N:2].[BH4-].[Na+]>CCO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9](=[O:30])[CH:10]([C:14]2[C:15]([F:29])=[CH:16][C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:27][OH:28])=[CH:18][C:19]=2[F:20])[O:11][CH2:12][CH3:13])=[CH:31][CH:32]=1)#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21904933HCID 21904933, compound

Product 1

HCID 21905518HCID 21905518, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of (RS)-N-(4-cyano-benzyl)-2-(3,5-difluoro-2′-formyl-biphenyl-4-yl)-2-ethoxy-acetamide (500 mg) in EtOH (1.2 ml) at 0° C. was added sodium borohydride (91 mg). After 5 min the ice bath was removed. Ice water was added and the mixture was extracted with EtOAc. The organic phase was dried, filtered and concentrated. The product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:2=>EtOAc) to give (RS)-N-(4-cyano-benzyl)-2-(3,5-difluoro-2′-hydroxymethyl-biphenyl-4-yl)-2-ethoxy-acetamide (413 mg). Colorless solid. MS 437.0 ([M+H]+)

Workup

  1. customAfter 5 min the ice bath was removed
  2. additionIce water was added
  3. extractionthe mixture was extracted with EtOAc
  4. customThe organic phase was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:2=>EtOAc)

Sources & evidence

ORD record
ord-2595bfdc9e1e489e889959023a3fbda5
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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