16417-32-6Relevant articles and documents
A practical and stereoselective synthesis of (+/-)-trans-4- benzyloctahydropyrrolo[3,4-b][1,4]oxazine
Walker, Daniel P.,Strohbach, Joseph W.,McGlynn, Molly A.,Lu, Hwang-Fun
, p. 1095 - 1103 (2010)
(Chemical Equation Presented) trans-Octahydropyrrolo[3,4-b][1,4]oxazine is an important heterocycle within the pharmaceutical industry for the preparation of biologically active analogs, including the phase III drug, finafloxacin. A practical synthesis of the title compound (2) is described in eight steps and ca. 10% overall yield. The key synthetic step is the formation of the pyrrolo[3,4-b][1,4]oxazine core 20 via a one pot double N-alkylation of the corresponding bis-tosylate 18 with 4-nitrobenzenesulfonamide. Subsequent removal of the nosyl group occurred under mild conditions.