Brucine → Brucine

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To (±)-3,5,5-trichloro-1,4-dihydroxycyclopent-2-ene-1-carboxylic acid (3) (A. W. Burgstahler, T. B. Lewis, and M. O. Abdel-Rahman, J. Org. Chem., 1966, 31, 3516; C. J. Moye and S. Sternhell, Aust. J. Chem., 1966 19, 2017) (10 g, 40.4 mmol) in methanol (1l) was added (-)-brucine (15.94 g, 40.4 mmol) in methanol (1l). Crystallisation at room temperature gave two crops (8.50 and 2.33 g respectively) of relatively pure (-)-brucine salt of the acid (4), [α]D25 - 110° (c 0.24, CHCl3). Recrystallisation from methanol gave the pure (-)-brucine salt of the acid (4) (9.64 g, 74%) as colourless plates, m.p. 143°-146°, [α]D25 -120° (c 0.247, CHCl3 ) (Found : C, 54.1; H, 4.85; Cl, 16.4; N, 4.05. C29H31Cl3N2O8 requires C, 54.25; H, 4.85; Cl 16.55; N, 4.35%).

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