Synthesis of 6?-Halogenodeoxyneopine from Neopine

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Abstract
(-)-Neopine (1), the Δ8,14 isomer of codeine, occurs as one of the minor constituents in opium from Papaver somniferum L1. In opium alkaloids of the morphine group the hydroxyl group in position 6 is readily converted with p-toluenesulfonyl chloride or methanesulfonyl chloride into the respective 6α-O-sulfonyl derivatives2. The latter in turn form starting materials for the preparation of other derivatives. Thus, with lithium halides, via a SN2 mechanism3 the 6β-halogen compounds are formed. It is found that, as a result of the allylic system, under slightly changed reaction conditions codeine itself can also yield the 8β-chloro derivative4.

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