Synthesis of piperidine derivatives fused to a tetrahydrofuran ring |
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Authors: | A I Moskalenko V I Boev |
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Institution: | 1. Lipetsk State Pedagogical University, ul. Lenina 42, Lipetsk, 398020, Russia 2. Timiryazev Russian State Agrarian University, Moscow, Russia
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Abstract: | Intramolecular nucleophilic opening of the oxirane ring in tert-butyl 6-(2-hydroxyethyl)-7-oxa-3-azabicyclo4.1.0]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-hydroxyhexahydrofuro2,3-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-hexahydrofuro2,3-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. |
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