tert-Butanol → Methyl 1-((tert-butoxycarbonyl)amino)cyclopropanecarboxylate

Participants

Reaction Conditions

Reaction Steps

A solution of 80 g of 1-(methoxycarbonyl)cyclopropanecarboxylic acid and 78 ml of triethylamine in 550 ml of toluene, to which 152 g of diphenylphosphoryl azide is added, is heated to 80° C. When the evolution of gas has ceased, the temperature is brought to 50° C. and 61 g of tert-butanol are added. After 7 hours' reaction at 80° C., the mixture is concentrated. The residue is taken up in ether, washed with saturated Na2CO3 solution, then with 1N hydrochloric acid solution, and then with NaHCO3 solution. After drying and evaporation of the organic phase, the residue is taken up in 300 ml of cyclohexane and then concentrated to dryness. The residue obtained is triturated in pentane, filtered and then dried, allowing the expected product to be isolated.

Provenance & Evidence