Methanesulfonyl chloride → HCID 558152, compound

Participants

Reaction Steps

To a solution of Compound (XIX) (0.22 g, 0.36 mmoles) in pyridine (15 mL), cooled at -10° C., methanesulfonyl chloride (0.03 mL, 0.39 mmoles) was added. After 6 days, the mixture was evaporated under reduced pressure. The resulting oil was treated with water (5 mL) and saturated aqueous sodium bicarbonate solution (20 mL), then extracted with ether (2×30 mL). The combined organic solution was dried over magnesium sulfate and the solvent evaporated under reduced pressure. Trituration of the resulting oil with ether yielded [1S-(1α,6β,7α,8β,9α,9aβ)]-octahydro-7,8,9-tris (phenylmethoxy)-6-[(phenylmethoxy)methyl]-2H-quinolizin-1-ol (XX) as white crystals (0.13 g, 60.8%) m.p. 103°-5° C.; IR (KBr) no absorbance 1650-1770 cm-1;MS (CI13 CH4) 594 (MH+), 486 (MH+ --PhCH2OH); 1H nmr (CDCl3) δ 1.2 (m, 1H), 1.4-1.6 (m, 3H), 1.8-2.0 (m, 2H), 2.6-2.8 (t, 1H), 3.0-3.1 (d, 1H), 3.2-3.3 (m, 1H), 3.5-3.9 (m, 4H), 4.2-5.0 (m, 9H), 7.1-7.4 (m, 20H).

Provenance & Evidence