Benzoyl chloride → HCID 53884909, compound

Participants

Reaction Steps

To a solution of Compound (XIII) (3.00 g; 4.40 mmoles) and triethyl amine (2.4 mL; 17.6 mmoles) in methylene chloride (25 mL), cooled at 0° C., was added benzoyl chloride (1.6 mL; 13.2 mmoles). The reaction was kept at room temperature for 16 hours, then water (5 mL) and saturated aqueous sodium bicarbonate solution (40 mL) were added. The phases were separated, and the aqueous phase was extracted with methylene chloride (30 mL). The combined organic solution was dried over sodium sulfate and the solvent evaporated under reduced pressure. The crude oil was purified via flash chromatography (silica gel; 1:4 ethyl acetate:hexane) to yield 3,4,5-tris(phenylmethoxy)-6-[(phenylmethoxy) methyl]-1-(phenylmethyl)-α-(2-propenyl)-2-piperidinemethanol benzoate (ester) (XIV) (1.92 g; 56%) as a clear, colorless oil and recovered Compound (XIII) (0.60 g; 0.88 mmoles). IR (neat) 1719 cm-1 (C=0); MS (FAB-MNBA) 788 (MH+), 680 (MH + --PhCH2OH); 1H nmr (CDCl3) δ 2.4 (m, 1H), 2.9 (dt, 1H), 3.5-4.0 (m, 8H), 4.1 (d, 1H), 4.4 (s, 2H), 4.5-4.9 (m, 9H), 5.4-5.6 (m, 1H), 7.1-7.4 (m, 27H), 7.5 (m, 1H), 8.1 (m, 2H).

Provenance & Evidence