Water → 4-Amino-1-(phenylmethyl)-3-pyrrolidinemethanol

HRID 1440110Notes

Reaction equation

HRID 1440110 reaction equation
[CH2:1]([N:8]1[CH2:12][C:11](=[N:13]O)[CH:10]([C:15](OCC)=[O:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].COCCO[Al+]OCCOC.[Na+].[H-].O>C1(C)C=CC=CC=1>[NH2:13][CH:11]1[CH:10]([CH2:15][OH:16])[CH2:9][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 86745294HCID 86745294, compound

Product 1

HCID 150238514-Amino-1-(phenylmethyl)-3-pyrrolidinemethanolYield 52.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 5.24 g (0.02 mole) of 1-benzyl-3-ethoxycarbonyl-4-hydroxyiminopyrrolidine [prepared as described in step (a) above] in 10 ml of toluene was added dropwise to 28 ml of a 3.4M solution of sodium bis(2-methoxyethoxy)aluminum hydride in toluene over a period of 1 hour. The mixture was stirred at room temperature for 1.5 hours and was then heated under reflux for 2 hours. At the end of this time, the reaction mixture was allowed to cool to room temperature, after which ice and water were added to it to form a precipitate, which was removed by filtration. The filtrate was concentrated by evaporation under reduced pressure, and the residue was purified by column chromatography through silica gel using methanol as the eluent, to afford 2.16 g of 3-amino-1-benzyl-4-hydroxymethylpyrrolidine as a brown oil.

Workup

  1. temperaturewas then heated
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool to room temperature
  4. customto form a precipitate, which
  5. customwas removed by filtration
  6. concentrationThe filtrate was concentrated by evaporation under reduced pressure
  7. customthe residue was purified by column chromatography through silica gel

Sources & evidence

ORD record
ord-f068676bc58140c3b5a8a2811ab70e35
Source dataset
uspto-grants-1996_03
Patent number
US05496951

Reaction notes

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