Triethylamine → HCID 54433857, compound

Participants

Reaction Steps

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°.

Provenance & Evidence