Ammonia → HCID 136030561, compound

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Reaction Steps

To 3.3 g of the acid obtained in Example 1, dissolved in 100 ml of tetrahydrofuran (THF), 1.6 g of carbonyldiimidazole is added and the mixture is stirred for 2 hrs. A solution is prepared of ammonia gas in 250 ml of anhydrous THF, into which the first solution obtained is introduced slowly. The mixture is stirred for 3 h and left to stand overnight. It is evaporated to dryness under reduced pressure and the residue is distributed between 150 ml of CH2Cl2 and 100 ml of water. The organic phase is decanted, dried over MgSO4, filtered and evaporated to dryness. An oil is obtained which is purified by chromatography on silica (eluent: ethyl acetate). The 3 final fractions containing the products are dried over MgSO4. The fractions are filtered and the filtrates evaporated to dryness. One of the 3 residues obtained, a mixture of both cis (32%) and trans (68%) isomers, is recrystallised in a mixture of ether and petroleum ether.

Provenance & Evidence