Sodium Hydroxide → 6-Benzyl-octahydropyrrolo[3,4-b][1,4]oxazine

HRID 36657Notes

Reaction equation

HRID 36657 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11](O)[CH:10]([NH:14][CH2:15][CH2:16][OH:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>S(=O)(=O)(O)O.O>[CH2:1]([N:8]1[CH2:12][CH:11]2[CH:10]([NH:14][CH2:15][CH2:16][O:17]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 19969797HCID 19969797, compound

Product 1

HCID 150699806-Benzyl-octahydropyrrolo[3,4-b][1,4]oxazine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

15.6 g (66mmol) of 1-benzyl-4-hydroxy-3-(2-hydroxyethylamino)-pyrrolidine are heated under reflux in a mixture of 60 ml of concentrated sulphuric acid and 20 ml of water for 6 hours. The mixture is rendered alkaline with concentrated sodium hydroxide solution, the sodium sulphate which has precipitated is filtered off with suction and the filtrate is extracted with chloroform. The extract is dried over potassium carbonate and concentrated and the residue is distilled.

Workup

  1. customthe sodium sulphate which has precipitated
  2. filtrationis filtered off with suction
  3. extractionthe filtrate is extracted with chloroform
  4. dry with materialThe extract is dried over potassium carbonate
  5. concentrationconcentrated
  6. distillationthe residue is distilled

Sources & evidence

ORD record
ord-fbb9da8152d3432bb09a0df0f86dab43
Source dataset
uspto-grants-1995_05
Patent number
US05416096

Reaction notes

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