(1S,3R,5S,6R)-6-ヒドロキシ-8-メチル-8-アザビシクロ[3.2.1]オクタン-3-イル 3-メチルブタノアート

説明An alkaloid found in Duboisia myoporoides, the base crystallizes from EtOH in colourless, nacreous plates and has [α]20D - 9.0° (c 5.0, EtOH), or - 4.0° (c 5.0, H2O). It yields a crystalline hydrobromide as colourless needles, m.p. l70-2°C; [α]20D + 5.0° (c 20.0, H20); picrate, m.p. lS2-3°C; methiodide, m.p. 20S.SoC and the acetyl derivative, characterized as the hydrobromide, m.p. 197°C. The isovaleryl ester forms a hydrochloride, m.p. l24-SoC; [α]D + 2.6° (c 3.78, EtOH) and a hydrobromide, m.p. l76-7°C. Treatment of the hydrobromide with thionyl chloride gives norvaleroidine due to demethylation, a colourless syrup which furnishes a crystalline hydrobromide, m.p. 270°C; [α]20D + 1 ° (c 20.0, H20). On hydrolysis with aqueous Ba(OHh, the base gives dihydroxytropane and isovaleric acid while oxidation with KMn04 furnishes norvalieroidine and a base C13H190 4N, m.p. 136°C; [α]20D - 16.6° (c 7.4, EtOH).