Reaction #1167

ord-7d193050015441f093d40bd7590a4914

Reaction equation

[Al+3].[H-].[H-].[H-].[H-].[Li+]
lithium aluminum hydride
COc1ccc2c(c1)OC(=O)[C@H]1CN(Cc3ccccc3)C[C@@H]21
cis-2-benzyl-7-methoxy-1,3,3a,9b-tetrahydrobenzopyrano[3,4-c]pyrrol-4-one
→
COc1ccc([C@H]2CN(Cc3ccccc3)C[C@H]2CO)c(O)c1
expected product
COc1ccc([C@H]2CN(Cc3ccccc3)C[C@H]2CO)c(O)c1
cis-1-Benzyl-3-hydroxymethyl-4-(2-hydroxy-4-methoxyphenyl)pyrrolidine

Reactants

[Al+3].[H-].[H-].[H-].[H-].[Li+]
lithium aluminum hydride
COc1ccc2c(c1)OC(=O)[C@H]1CN(Cc3ccccc3)C[C@@H]21
cis-2-benzyl-7-methoxy-1,3,3a,9b-tetrahydrobenzopyrano[3,4-c]pyrrol-4-one

Reagents

None

Solvents

C1CCOC1
THF

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherdescribed in Preparation G, at +5° C
  2. 2
    TemperatureThe reaction medium is maintained at +10° C. for one hour
  3. 3
    Filtrationis filtered on Celite
  4. 4
    OtherThe organic phase is dried
  5. 5
    Otherafter evaporation

Procedure

To 230 mmol of lithium aluminum hydride in 800 ml of THF, under a nitrogen atmosphere, are added 180 mmol of cis-2-benzyl-7-methoxy-1,3,3a,9b-tetrahydrobenzopyrano[3,4-c]pyrrol-4-one, described in Preparation G, at +5° C. The reaction medium is maintained at +10° C. for one hour before being hydrolyzed, and is filtered on Celite. The organic phase is dried and, after evaporation, gives the expected product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723484uspto-grants-1998_03