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[reaction: see text] Primary amines reacted with carbonate salts (Na2CO3, K2CO3, Cs2CO3, and Ag2CO3) and halomethyloxiranes in the presence of a base such as DBU or TEA to give oxazolidinones in high yields. The use of K2CO3 among these carbonate gave the best yield in this synthesis. A reaction mechanism was proposed that the oxazolidinone was obtained from an oxazinanone intermediate via a bicyclo[2.2.1] intermediate. The present reaction can be widely applied to convenient synthesis of useful N-substituted oxazolidinones and chiral oxazolidinones.

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An analog of nor-binaltorphimine (nor-BNI) without the 4,5-epoxy bridge, 17,17-bis(cyclopropylmethyl)-6,6,7,7-tetrahydro-6,6-imino-14b b,14a a-dihydroxy-3,3-dimethoxy-7,7-bimorphinan (4), which was the precursor of the designed compound 1 as a selective k k 3 opioid receptor antagonist, was catalytically oxidized with oxygen in the presence of platinum to give the 5-oxo derivative 3 with some other oxidized products. Morphinan derivatives without the 4,5-epoxy moiety were labile to oxygen, although the corresponding 4,5-epoxymorphinan derivatives resisted aerobic oxidation. One of the oxidized nor-BNI analogs without 4,5-epoxy bridge, compound 18, showed high affinity and selectivity for k k opioid receptor.