反应 #309679

ord-cff4338f9c0b418ea107075245d3082a

反应方程式

O=CCc1ccccc1
phenylacetaldehyde
NCCc1ccccc1
2-phenylethylamine
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
sodium triacetoxy-borohydride
c1ccc(CCNCCc2ccccc2)cc1
compound D
收率 11.0%
c1ccc(CCNCCc2ccccc2)cc1
Diphenethylamine
收率 11.0%

溶剂

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他The solution is quenched with aq. saturated sodium bicarbonate (200 mL)
  2. 2
    萃取extracted with EtOAc (4×100 mL)
  3. 3
    其他dried
  4. 4
    浓缩concentrated under vacuum
  5. 5
    其他The residue is purified by flash chromatography (silica gel; EtOAc/MeOH 9:1)

实验过程

To a solution of phenylacetaldehyde (6.0 g, 50 mmol) and 2-phenylethylamine in THF (200 mL) is added sodium triacetoxy-borohydride drop wise. The solution is stirred under nitrogen overnight at room temperature. The solution is quenched with aq. saturated sodium bicarbonate (200 mL), and extracted with EtOAc (4×100 mL). The organic extracts are combined, dried and concentrated under vacuum. The residue is purified by flash chromatography (silica gel; EtOAc/MeOH 9:1) to provide 1.25 g (11%) of the compound D as a clear oil. M+H+=226.10.

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US08207183B2uspto-grants-2012_06