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

HRID 1528795Notes

Reaction equation

HRID 1528795 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-phenethyl-amine (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-04eeffc8b4d24d33a8222decffa51435
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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