Reacción #1637

ord-c88884b2244548bda021d31a20f133fd

Ecuación de reacción

Oc1ccc(CCNC[C@H](O)COc2ccc(OCc3ccccc3)cc2)cc1
(S)-1-(4-benzyloxyphenoxy)-3-[N-2-(4-hydroxyphenyl)ethylamino]propan-2-ol
BrCc1ccccc1
benzyl bromide
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
Oc1ccc(CCN(Cc2ccccc2)C[C@H](O)COc2ccc(OCc3ccccc3)cc2)cc1
title compound
Oc1ccc(CCN(Cc2ccccc2)C[C@H](O)COc2ccc(OCc3ccccc3)cc2)cc1
(S)-N-Benzyl-1(4-benzyloxyphenoxy)-3-[N-2-(4-hydroxyphenyl)ethylamino]propan-2-ol

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    FiltraciónThe mixture was filtered
  2. 2
    Lavadothe residue was washed with ethyl acetate
  3. 3
    Lavadowashed with water and brine
  4. 4
    Otrodried
  5. 5
    Otroevaporated
  6. 6
    OtroPurification of the residue by flash chromatography (silica gel, 50% ethyl acetate in hexane)

Procedimiento

A solution of (S)-1-(4-benzyloxyphenoxy)-3-[N-2-(4-hydroxyphenyl)ethylamino]propan-2-ol (1.9 g, 4.8 mMol) and benzyl bromide (0.57 ml, 4.8 mMol) in dimethylformamide (10 ml) containing sodium carbonate (770 mg, 7.2 mMol) was stirred at room temperature for 18 hours. The mixture was filtered and the residue was washed with ethyl acetate. The filtrates were combined, washed with water and brine, dried and evaporated. Purification of the residue by flash chromatography (silica gel, 50% ethyl acetate in hexane) gave the title compound.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05726165uspto-grants-1998_03