Sodium cyanoborohydride → HCID 54283156, compound

HRID 1087796Notes

Reaction equation

HRID 1087796 reaction equation
C([BH3-])#N.[Na+].[CH3:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:7]=1[N:13]1[CH:17]=[CH:16][C:15]([C:18](=[N:20][OH:21])[CH3:19])=[CH:14]1>CO.Cl>[OH:21][NH:20][CH:18]([C:15]1[CH:16]=[CH:17][N:13]([C:7]2[C:8]([CH3:12])=[CH:9][CH:10]=[CH:11][C:6]=2[CH3:5])[CH:14]=1)[CH3:19]

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 86744248HCID 86744248, compound

Product 1

HCID 54283156HCID 54283156, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Two mole-equivalents of sodium cyanoborohydride is added to a mixture of 1-(2,6-dimethylphenyl-3-acetyl-1H-pyrrole oxime in methanol and ethanolic hydrochloric acid is added to adjust to pH 3. The reaction mixture is stirred at room temperature overnight, poured over ice, rendered basic and extracted with ether. The ether extract is washed with brine, dried and evaporated to dryness. The residue is chromatographed over silica gel by gradient elution with methylene chloride/methanol, to yield N-hydroxy-1-[1-(2,6-dimethylphenyl)-1H-pyrrol-3-yl]-ethylamine.

Workup

  1. additionis added
  2. additionpoured over ice
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washis washed with brine
  6. customdried
  7. customevaporated to dryness
  8. customThe residue is chromatographed over silica gel by gradient elution with methylene chloride/methanol

Sources & evidence

ORD record
ord-756ac94e5db84097a7140a7e6cb4d1bb
Source dataset
uspto-grants-1990_10
Patent number
US04960787

Reaction notes

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