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

HRID 981071Notes

Reaction equation

HRID 981071 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. 4,254,135) 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-ec84cea7a1794c7eb87ff7d58c2fb1a2
Source dataset
uspto-grants-1991_02
Patent number
US04990517

Reaction notes

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