Water → [5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-ylmethyl]-methyl-phenethyl-amine

HRID 1512584Notes

Reaction equation

HRID 1512584 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH:14]=O)=[CH:4][CH:3]=1.[CH3:16][NH:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[BH4-].[Na+].O>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[C:9]=2[CH2:14][N:17]([CH3:16])[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11503N-MethylbenzeneethanamineHCID 4311764Sodium borohydrideHCID 821337925-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde

Product 1

HCID 66577314[5-(4-Bromo-phenyl)-3-methyl-isoxazol-4-ylmethyl]-methyl-phenethyl-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(4-Bromo-phenyl)-3-methyl-isoxazole-4-carbaldehyde (0.150 g, 0.56 mmol) and N-methyl-phenethylamine (0.10 mL, 0.67 mmol) were combined in MeOH and stirred at room temperature overnight. Once no starting material was seen by analytical LCMS, sodium borohydride (0.064 g, 1.69 mmol) was added and the reaction was stirred at room temperature for 1 hour. H2O was added and the mixture was extracted with EtOAc. The combined organic layers were dried and concentrated, and the residue was purified by silica gel chromatography to give the title compound.

Workup

  1. additionwas added
  2. stirringthe reaction was stirred at room temperature for 1 hour
  3. extractionthe mixture was extracted with EtOAc
  4. customThe combined organic layers were dried
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a322bef512624e45a1aaa32b65d2ed50
Source dataset
uspto-grants-2012_07
Patent number
US08217066B2

Reaction notes

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