Reacción #1166

ord-aad0c6cdb96e435783b60b50f263f74c

Ecuación de reacción

[Cl-].[Na+]
sodium chloride
CC(C)O
isopropyl alcohol
[Al+3].[H-].[H-].[H-].[H-].[Li+]
lithium aluminum hydride
COC(=O)[C@@H]1CN(Cc2ccccc2)C[C@H]1c1ccccc1OC
methyl [trans-1-benzyl-4-(2-methoxyphenyl)pyrrolidin-3-yl]carboxylate
COc1ccccc1[C@@H]1CN(Cc2ccccc2)C[C@H]1CO
expected product
COc1ccccc1[C@@H]1CN(Cc2ccccc2)C[C@H]1CO
trans-1-Benzyl-3-hydroxymethyl-4-(2-methoxyphenyl)pyrrolidine

Condiciones de reacción

Temperatura
5°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrodescribed in Preparation A)
  2. 2
    workup.STIRRINGThe mixture is stirred slowly at room temperature
  3. 3
    FiltraciónAfter filtration and evaporation of the solvents

Procedimiento

To 560 mmol of lithium aluminum hydride in 800 ml of tetrahydrofuran (THF), under a nitrogen atmosphere and at 5° C., are added 225 mmol of methyl [trans-1-benzyl-4-(2-methoxyphenyl)pyrrolidin-3-yl]carboxylate (described in Preparation A) dissolved in 500 ml of THF. After stirring for 1 hour at 5° C., 139 ml of isopropyl alcohol are added slowly to the above mixture, followed by 85.2 ml of saturated sodium chloride solution. The mixture is stirred slowly at room temperature. After filtration and evaporation of the solvents, the expected product is obtained.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05723484uspto-grants-1998_03