Aluminium lithium hydride → cis-1-Benzyl-3-hydroxymethyl-4-(2-hydroxy-4-methoxyphenyl)pyrrolidine

HRID 1071

Reaction equation

HRID 1071 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:18][C@H:17]2[C:19]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:20]=3[O:21][C:22](=[O:23])[C@H:16]2[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([N:14]1[CH2:18][C@H:17]([C:19]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][C:20]=2[OH:21])[C@H:16]([CH2:22][OH:23])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22882984cis-2-Benzyl-7-methoxy-1,3,3a,9b-tetrahydrobenzopyrano[3,4-c]pyrrol-4-one

Product 1

HCID 70343980cis-1-Benzyl-3-hydroxymethyl-4-(2-hydroxy-4-methoxyphenyl)pyrrolidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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.

Workup

  1. customdescribed in Preparation G, at +5° C
  2. temperatureThe reaction medium is maintained at +10° C. for one hour
  3. filtrationis filtered on Celite
  4. customThe organic phase is dried
  5. customafter evaporation

Sources & evidence

ORD record
ord-7d193050015441f093d40bd7590a4914
Source dataset
uspto-grants-1998_03
Patent number
US05723484

Linked notes

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