Dimethylamine, reaction with lactones

The cyanobromide (371) was condensed with the bc portion (347) to give the thioether (372) sulfide contraction to give (373) was accomplished using tris(/3-cyanoethyl) phosphine, and with phosphorus pentasulfide the thiolactam-thiolactone (374) was produced. After treatment with Meerwein s salt, reaction with dimethylamine opened the lactone with concomitant formation of an exocyclic methylene group, and subsequent treatment with cobalt chloride or iodide gave the chelate (375) which was reacted with diazabicyclononane to give bisnorcobyrinic add [Pg.435]

Just as amines react with esters to form amides, lactones react with amines to give lactams or are opened to give amino acid derivatives directly. When P-propiolactone (2.20) reacted with ammonia, for example, 3-aniinopropanamide (2.2Ia) was obtained. 2 Similar reaction with methylamine gaveno2.2/h but rather a 97% yield of 3-aminopropanoic acid, 2.22. Dimethylamine, however, converted 2.20 to 2.2Ic in 79% yield, along with 13% of 2.22.12... 

In an alternative synthesis,3 a methoxycarbonyl lactone, for example (5), is treated successively with formaldehyde-dimethylamine hydrochloride (Mannich reaction), methyl iodide, and finally heated in dimethylformamide. The final step... 

Opening of the epoxide 101 with dimethylamine leads to two regioiso-meric dimethylamino alcohols, 104 and 105, in a ratio of 4 1. Catalytic hydrogenation of 104, lactonization by means of acetic anhydride, and DIBAH reduction of the lactone 106 completed a synthesis of racemic form of another antibiotic sugar, forosamine (107, 2,3,4,6-tetradeoxy-4-dimethylamino-DL-er-yf/iro-hexopyranose). When the starting epoxide 101 was resolved by means of its (-I- )-phenylethylammonium salt into enantiomers, the same reaction sequence... 

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