136749-80-9Relevant articles and documents
Synthesis of (+/-)-6-Alkyl-5-oxa-1-azabicyclononan-9-ones, (+/-)-5-Alkyl-4-oxa-1-azabicyclooctan-8-ones, and Substituted 1,6-Dioxa-3,8-diazacyclodecanes by Reaction of Ethyl 4-Oxoalkanoates with 3-Aminopropanol and 2-Aminoethanol
Wedler, Christine,Schick, Hans,Scharfenberg-Pfeiffer, Doris,Reck, Guenter
, p. 29 - 32 (2007/10/02)
Ethyl 4-oxoalkanoates 1 react at ambient temperature in dry methanol in the presence of molecular sieve 3 Angstroem in almost quantitative yield with 3-aminopropanol and 2-aminoethanol to form the bicyclic lactams rac-2 and rac-3, respectively.Surprisingly, the (+/-)-5-alkyl-4-oxa-1-azabicyclooctan-8-ones rac-3a-d dimerize in trichloromethane saturated with 2 N HCl to the ten-membered heterocycles 4a-d.The structures of the substituted 1,6-dioxa-3,8-diazacyclodecanes 4a and 4c have been determined by an X-ray crystal analysis. Key Words: 4-Oxoalkanoates, ethyl- / 5-Oxa-1-azabicyclononan-9- ones, (+/-)-6-alkyl- / 4-Oxa-1-azabicyclo-octan-8-ones, (+/-)-5-alkyl- / 1,6-Dioxa-3,8-diazacyclodecanes