Journal of Organic Chemistry 2003-03-07

Practical and high-yield syntheses of dihydromorphine from tetrahydrothebaine and efficient syntheses of (8S)-8-bromomorphide.

Anna K Przybyl, Judith L Flippen-Anderson, Arthur E Jacobson, Kenner C Rice

Index: J. Org. Chem. 68(5) , 2010-3, (2003)

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Abstract

A practical method for the conversion of tetrahydrothebaine to dihydromorphine in 92% yield is described. The procedure should allow more efficient production of opium products and may be easily modified for large-scale synthesis. The conversion of codeine to (8S)-8-bromomorphide, a potentially valuable intermediate to 6-demethoxyoripavine and derivatives, is also described. The absolute configuration of (8S)-8-bromomorphide was determined by a single-crystal X-ray diffraction study of the hydrobromide salt.