Preparation of (f)-Laudaniae (1V) from I-Sodium borohydride (0.1 9.) was added in portjons to a solution of I (0.1 8.) in ethanol and the mixture was stirred at room temperature for 3 hr. Methanol was added and after 30 min. the reaction mixture was evaporated to dryness. The residue was dissolved in water and extracted with ether. The ether extracts were dried and evaporated to yield a residue which crystallized from methanol as white prisms of IV, m.p. 166-168"; A:''' 230 and 283 nm. (log 4.08 and 3.78); positive FeCI, test, violet Burger test; mass spectrum: m/e 343 (I), 342(5). 327(2), 206(100), 204(8), 192(40), 190(80), 174(8), 162(36), and 137(19); NMR(CDC13): 62.52 s (3H, N-CHs), 3.58 s(3H,C-7. C-5H), 6.52 and 6.73 AB quartet (2H, J = 8 Hz., C-2', C-3'H), and 6.75 broad s (IH, C-5'H); (+)-laudanine lit. ( I ) m.p. 166-167", Burger test: violet color (I).
Interconversion of Palaudine and I-A solution of V (3 mg.) and methyl iodide (0.1 ml.) in ethanol (2 ml.) was allowed to stand for 18 hr. It was evaporated and passed through an ion-exchange column (CI-form) using ethanol-acetone. The residue was crystallized from ethanol as needles (4 mg.), m.p. 231-233'. Palaudine methochloride and I were indistinguishable in terms of the R, values OCHa), 3.85~(6H,C-6,C-4',OCHs), 6.08~(lH,C-8H), 6.58s(lH, and UV spectra, and no mixed melting-point depression was observed.