Cyclohexene → HCID 54355047, compound

Participants

Reaction Steps

To a solution of Compound (XV) (0.60 g; 0.74 mmoles) and cyclohexene (5 mL) in methanol (30 mL), Pearlman's catalyst (0.2 g) was added under a nitrogen atmosphere. The suspension was stirred at room temperature for 18 hours, then the catalyst was filtered through Celite and washed with methanol (20 mL). The combined organic layer was evaporated under reduced pressure to yield a crude oil, which was purified via flash chromatography (silica gel; 1:1 as a clear colorless oil (0.34 g) and recovered Compound (XV) (0.10 g; 16% recovery). The N-debenzylated alcohol (0.34 g) was dissolved in pyridine (20 mL) and cooled to -10° C., then methanesulfonyl chloride (0.04 mL) was added, and reaction was continued for 96 hours. The solvent was evaporated under reduced pressure and saturated aqueous sodium bicarbonate solution was added to the residue. After extraction with ether (2×60 mL), the combined organic solution was dried over magnesium sulfate and the solvent evaporated under reduced pressure. The crude product was purified via flash chromatorgraphy (silica gel; 1:1 ethyl acetate:hexane) to yield Octahydro-7,8,9-tris (phenylmethoxy)-6-[(phenylmethoxy)methyl]-2H-quinolizin1-ol benzoate (ester) (XVI) (0.16 g; 50%) as a colorless oil. IR (film from CDCl3) 1718 cm-1 (C=0); MS(CI--CH4) 698 (MH+), 576 (MH+ -PhCO2H); 1H nmr (CDCl3) δ 1.2 (m, 1H), 1.6-1.9 (m, 2H), 2.2 (d, 1H), 2.8 (t, 1H), 3.3-3.4 (m, 2H), 3.5-3.7 (m, 3H), 3.8 (m, 1H), 4.1 (t, 1H), 4.3 (d, 1H), 4.4-4.7 (m, 7H), 4.9 (d, 1H), 5.5 (s, 1H), 7.0-7.4 (m, 22H), 7.5 (m, 1H), 8.1 (m, 2H).

Provenance & Evidence