Sodium Hydroxide → 7-Benzyl-1-oxa-4,7-diazaspiro[5.4]decane

HRID 8575Notes

Reaction equation

HRID 8575 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10](O)(CNCCO)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:19].[Na+]>S(=O)(=O)(O)O.O>[CH2:1]([N:8]1[CH2:9][CH2:10][CH2:11][C:12]21[O:19][CH2:2][CH2:1][NH:8][CH2:9]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 219835141-Benzyl-3-(((2-hydroxyethyl)amino)methyl)pyrrolidin-3-ol

Product 1

HCID 219835427-Benzyl-1-oxa-4,7-diazaspiro[5.4]decane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
180 °C

Procedure

85.0 g (340 mmol) of 1-benzyl-3-hydroxy-3-(2-hydroxyethylaminomethyl)-pyrrolidine are dissolved in a mixture of 280 ml of concentrated sulfuric acid and 140 ml of water and heated at 180° C. overnight. The mixture is made alkaline with 45% strength sodium hydroxide solution, precipitated salts are dissolved in water, and the solution is extracted five times with 200 ml of chloroform each time. The organic phases are dried over potassium carbonate, the desiccant is removed, and the solution is concentrated. The residue is distilled under high vacuum. 60.0 g (76% of theory) of the product are obtained.

Workup

  1. customprecipitated salts
  2. dissolutionare dissolved in water
  3. extractionthe solution is extracted five times with 200 ml of chloroform each time
  4. dry with materialThe organic phases are dried over potassium carbonate
  5. customthe desiccant is removed
  6. concentrationthe solution is concentrated
  7. distillationThe residue is distilled under high vacuum
  8. custom60.0 g (76% of theory) of the product are obtained

Sources & evidence

ORD record
ord-28fe674f09774641b55817670fb93e9a
Source dataset
uspto-grants-2006_08
Patent number
US07091198B1

Reaction notes

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