Water → 1-Benzyl-3-hydroxymethyl-3-methoxypyrrolidine

HRID 1681616Notes

Reaction equation

HRID 1681616 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1([O:23][CH3:24])[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12]1)=O.O.[OH-].[K+]>C(OCC)C>[CH2:16]([N:13]1[CH2:14][CH2:15][C:11]([CH2:9][OH:8])([O:23][CH3:24])[CH2:12]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14797Potassium HydroxideHCID 21226445Aluminium lithium hydrideHCID 537153081-Benzyl-3-methoxypyrrolidine-3-carboxylic acid methylester

Product 1

HCID 193821711-Benzyl-3-hydroxymethyl-3-methoxypyrrolidine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

6.5 g Lithium aluminum hydride are suspended in 250 ml of dry diethylether. 42 g (0.16 mol) 1-benzyl-3-methoxypyrrolidine-3-carboxylic acid methylester are added dropwise. The mixture is stirred for 2 hours under reflux. Thereafter 6.5 ml of water, 6.5 ml 15% proof KOH and 6.5 ml of water are added, the inorganic salts are removed by filtration and washed twice with tetrahydrofuran. The organic solvents are removed from the filtrate in vacuo and the residue is distilled.

Workup

  1. temperatureunder reflux
  2. customthe inorganic salts are removed by filtration
  3. washwashed twice with tetrahydrofuran
  4. customThe organic solvents are removed from the filtrate in vacuo
  5. distillationthe residue is distilled

Sources & evidence

ORD record
ord-337129c626bf41b59ca48b323e4f707d
Source dataset
uspto-grants-1992_12
Patent number
US05173484

Reaction notes

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