Sodium borohydride → HCID 19744527, compound

HRID 2254400Notes

Reaction equation

HRID 2254400 reaction equation
[CH3:1][C:2]([CH3:28])([CH3:27])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]=[O:26])[CH:20]=2)[CH:12]=1)[CH3:9].[BH4-].[Na+]>C(O)C>[CH3:1][C:2]([CH3:28])([CH3:27])[C:3]#[C:4]/[CH:5]=[CH:6]/[CH2:7][N:8]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][OH:26])[CH:20]=2)[CH:12]=1)[CH3:9]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19744731HCID 19744731, compound

Product 1

HCID 19744527HCID 19744527, compoundYield 46.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

85 mg of the (E)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-3-(3-formylbenzyloxy)benzylamine obtained as above was dissolved in 2 ml of ethanol, and under ice cooling, 8.6 mg of sodium borohydride was added with stirring for 30 minutes. The solvent was evaporated under reduced pressure. The residue was dissolved in a mixture of ethyl acetate and water. The organic layer was separated, and dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, and the solvent was evaporated. The residue was purified by silica gel column chromatography (Wakogel C-200, 15 g; eluting solvent: hexane/ethyl acetate=10/1→5/1) to give 40 mg (yield 39%) of the captioned compound as a colorless oil.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in a mixture of ethyl acetate and water
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe desiccant was removed by filtration
  6. customthe solvent was evaporated
  7. customThe residue was purified by silica gel column chromatography (Wakogel C-200, 15 g; eluting solvent: hexane/ethyl acetate=10/1→5/1)

Sources & evidence

ORD record
ord-8852bf693da548d6bf8ef4d2cc0b614a
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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