LUPANOLINE

Description

This isomer of Hydroxylupanine occurs in Lupinus sericeus Pursh. It is dextrorotatory with [α]²³_D+ 31 ° (c 0.726, EtOH) or + 64.4° (c 0.88, H20). The base forms stout, colourless prisms from Me2CO and yields a hydrochloride, m.p. 27 5-6°C and a methiodide as long, colourless needles from MeOH, m.p. 230- 1°C. With LiAIH4 in dioxan it gives a:-isosparteine as a colourless oil, b.p. 110- 120°CjI mm, characterized as the perchlorate, m.p. 255°C (dec.). Refluxing with AC20 furnishes the anhydro base, a colourless oil, m.p. 145-150°C/0.I mm which readily crystallizes on standing to form colourless prisms, m.p. 94-5°C; [α]²⁴_D - 43.1 ° (c 0.58, H20) and characterized as the perchlorate, m.p. 252-3°C (dec.); [α]²⁶_D - 57° (c 0.912, H20). The anhydro base may be hydrogenated with Pt02 as catalyst to give dihydroanhydrolupanoline, colourless sheaves of crystals, m.p. I 03-4°C, giving a perchlorate, m.p. 224-5°C.

References

Marion, Leonard, Moore., Can. J. Chern., 31, 181 (1953)