Sodium Bicarbonate → HCID 16771440, compound

HRID 636741Notes

Reaction equation

HRID 636741 reaction equation
[F:1][C:2]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:3]=1[CH:4]=[N:5][C:6]([CH3:9])([CH3:8])[CH3:7].[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO>[F:1][C:2]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:3]=1[CH2:4][NH:5][C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 21255693HCID 21255693, compound

Product 1

HCID 16771440HCID 16771440, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the obtained N-(2,4-difluorobenzylidene)-t-butylamine in methanol (5 ml) was cooled to 0° C. in ice-water bath. To the solution was added NaBH4 (138.3 mg, 3.65 mmol). The mixture was gradually warmed to room temperature and stirred for 2.5 hours. The mixture was added to sat. NaHCO3 aqueous solution, extracted three times with ethyl acetate and dried over MgSO4. The mixture was concentrated and purified by silica gel chromatography (hexane/ethyl acetate/triethylamine=100/5/1) to give the title compound (504.2 mg; 83%, 2 steps).

Workup

  1. extractionextracted three times with ethyl acetate
  2. dry with materialdried over MgSO4
  3. concentrationThe mixture was concentrated
  4. custompurified by silica gel chromatography (hexane/ethyl acetate/triethylamine=100/5/1)

Sources & evidence

ORD record
ord-4c79521260bf456abbab4f62e00715c2
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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