Boron trifluoride etherate → HCID 20069137, compound

HRID 982041Notes

Reaction equation

HRID 982041 reaction equation
B(F)(F)F.CCOCC.[C:10]1([CH2:16][CH2:17][C:18]([NH:20][C:21]2[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=2[C:23]([O:25][CH3:26])=[O:24])=O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[BH4-].[Na+]>COCCOC>[C:10]1([CH2:16][CH2:17][CH2:18][NH:20][C:21]2[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=2[C:23]([O:25][CH3:26])=[O:24])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 903133HCID 903133, compoundHCID 4311764Sodium borohydride

Product 1

HCID 20069137HCID 20069137, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

3.4 ml of boron trifluoride etherate are added to a solution of 5.6 g of methyl 2-(3-phenylpropanoylamino)benzoate in 35 ml of anhydrous 1,2-dimethoxyethane. After cooling to 0° C., 3.4 g of sodium borohydride are added in portions, while stirring and cooling, and then the mixture is stirred at 60° C. for 45 hours and, after cooling, is poured onto ice-water. Extraction with ethyl acetate, evaporation off of the solvent and column chromatography of the residue as described under (a) provides methyl 2-(3-phenylpropylamino)benzoate.

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at 60° C. for 45 hours
  3. temperatureafter cooling
  4. additionis poured onto ice-water
  5. extractionExtraction
  6. customwith ethyl acetate, evaporation off of the solvent and column chromatography of the residue

Sources & evidence

ORD record
ord-817bbab32185427c89dac96818804892
Source dataset
uspto-grants-1991_02
Patent number
US04994493

Reaction notes

Loading…