Triethylamine → HCID 54433857, compound

HRID 1283138Notes

Reaction equation

HRID 1283138 reaction equation
[OH:1][C:2]1([CH:14]([CH3:18])C(O)=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C([N:21]([CH2:24]C)CC)C.ClC(OCC)=[O:28].[N-]=[N+]=[N-].[Na+]>CC(C)=O.O>[CH3:18][CH:14]1[C:2]2([CH2:7][CH2:6][CH2:5][CH2:4][CH:3]2[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:1][C:24](=[O:28])[NH:21]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33557Sodium AzideHCID 21519247HCID 21519247, compound2×

Product 1

HCID 54433857HCID 54433857, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

2-(1-Hydroxy-2-phenylcyclohexyl) propionic acid (Example II, Compound I) (33 g) in 110 ml acetone is teated with 20.5 ml triethylamine. The solution is cooled to -5° and 14 ml ethyl chloroformate in 35 ml acetone added at a temperature below 0°. The mixture is stirred 10 minutes and 17.2 g of sodium azide in 50 ml water is added at or below 0°. The mixture is stitted 11/2 hours, added to 500 ml ice water and extracted with toluene. The extract is dried and heated at 100° until the evolution of nitrogen is above over, then refluxed 2 hours, concentrated to a slurry on the rotovap and the solid filtered and washed with benzene and cyclohexane to give 28.8 g of 4-methyl-6-phenyl-1-oxa-3-azaspiro [4.5] decan-2-one, m. 171°-3°.

Workup

  1. temperatureThe solution is cooled to -5°
  2. custom2 hours
  3. extractionextracted with toluene
  4. customThe extract is dried
  5. temperatureheated at 100° until the evolution of nitrogen
  6. temperaturethen refluxed 2 hours
  7. concentrationconcentrated to a slurry on the rotovap
  8. filtrationthe solid filtered
  9. washwashed with benzene and cyclohexane

Sources & evidence

ORD record
ord-be9eec6e91f0412290c19c15c3ba702a
Source dataset
uspto-grants-1976_08
Patent number
US03974157

Reaction notes

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