A. I. Moskalenko, V. Boev
Feb 14, 2014
Citations
0
Influential Citations
3
Citations
Journal
Russian Journal of Organic Chemistry
Abstract
Intramolecular nucleophilic opening of the oxirane ring in tert-butyl 6-(2-hydroxyethyl)-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate by the action of excess potassium hydroxide in 75% aqueous dimethyl sulfoxide at 110–120°C gave tert-butyl (3aR,7aS)-3a-hydroxyhexahydrofuro[2,3-c]pyridine-6(2H)-carboxylate whose treatment with POCl3 resulted in elimination of water molecule and tert-butoxycarbonyl group with formation of 2,3,4,5,6,7-hexahydrofuro[2,3-c]pyridine hydrochloride. The latter reacted with electrophiles (acetic anhydride, methanesulfonyl chloride, and benzaldehyde in combination with sodium triacetoxyhydridoborate) in the presence of triethylamine, yielding the corresponding N-substituted 2,3,4,5,6,7-hexahydrofuro[ 2,3-c]pyridine derivatives.