tert-Butanol → 3-Tert-butoxycarbonylamino-beta-carboline

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Reaction Steps

0.25 g of β-carboline-3-carboxylic acid are dissolved in 4 ml of dimethylsulfoxide while being heated. 10 ml of tert-butanol, 0.25 ml of diphenylphosphoryl azide and 0.17 ml of triethylamine are added to the solution. The reaction mixture is refluxed for 15 minutes. The crystals precipitated during cooling are filtered off, the tert-butanol is evaporated from the filtrate under vacuum and the residue is mixed with 10 ml of water. 0.025 g of 3-tert-butoxycarbonylamino-β-carboline with a 185°-190° C. melting point (methanol) is obtained from the resulting precipitate by chromatography on silica gel (methylene chloride with 5% methanol).

Provenance & Evidence