Acetic Acid → trans-1-Benzyl-3-hydroxy-4-methoxypyrrolidine

HRID 974884Notes

Reaction equation

HRID 974884 reaction equation
[CH2:1]([N:8]1CC2[CH:10]([O:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][O-].[Na+].[C:17]([OH:20])(=O)[CH3:18]>CO>[CH2:1]([N:8]1[CH2:18][C@@H:17]([O:20][CH3:14])[C@H:10]([OH:11])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 98153703-Benzyl-6-oxa-3-azabicyclo(3.1.0)hexaneHCID 10942334Sodium Methoxide

Product 1

HCID 15069965trans-1-Benzyl-3-hydroxy-4-methoxypyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

34.9 g (0.2 mol) of 3-benzyl-6-oxa-3-azabicyclo[3.1.0]hexane (U.S. Pat. No. 4,0254,135) are heated with 3.6 g (20 mmol) of sodium methylate solution (30% strength) at 120° C. in 200 ml of absolute methanol in an autoclave for 10 hours. After cooling, the mixture is neutralized with 1.2 g (20 mmol) of acetic acid and the solvent is removed on a rotary evaporator. The residue is taken up in tetrahydrofuran and the sodium acetate is filtered off. The filtrate is concentrated and the residue is distilled.

Workup

  1. temperatureAfter cooling
  2. customthe solvent is removed on a rotary evaporator
  3. filtrationthe sodium acetate is filtered off
  4. concentrationThe filtrate is concentrated
  5. distillationthe residue is distilled

Sources & evidence

ORD record
ord-45e0668fec7c4f3e8d89695ea82bf871
Source dataset
uspto-grants-1997_03
Patent number
US05607942

Reaction notes

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