Réaction #1166

ord-aad0c6cdb96e435783b60b50f263f74c

Équation de réaction

[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

Réactifs

[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

Réactifs

Aucun

Solvants

C1CCOC1
THF
C1CCOC1
tetrahydrofuran

Conditions de réaction

Température
5°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

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

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05723484uspto-grants-1998_03