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

HRID 2400090Notes

Reaction equation

HRID 2400090 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 acidmethylester 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 tetrahydrofurane. The organic solvents are removed from the filtrate in vacuo and the resedue is destilled.

Workup

  1. temperatureunder reflux
  2. customthe inorganic salts are removed by filtration
  3. washwashed twice with tetrahydrofurane
  4. customThe organic solvents are removed from the filtrate in vacuo

Sources & evidence

ORD record
ord-e479d28f8ede4f83b77c5d2b649a67eb
Source dataset
uspto-grants-1995_09
Patent number
US05453422

Reaction notes

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