Benzyl Alcohol → HCID 57228780, compound

Participants

Reaction Conditions

Reaction Steps

[1R *,8S*,9aR*]5,6-Dimethoxy-8-phenyl-2,3,7,8,9,9a-hexahydrophenalene-1-carboxylic acid (0.8 g, 2.3 mmol), from Step 5, and triethylamine (0.32 mL, 2.3 mmol) were dissolved in 16 mL of toluene and 0.55 mL (2.5 mmol) of diphenylphosphoryl azide was added. The reaction mixture was heated at 80° C. for 2.5 h then 0.5 mL (4.8 mmol) of benzyl alcohol was added and heating was continued at 80° C. for an additional 3 h and at 65° C. for 15 h. The reaction mixture was cooled and concentrated under reduced pressure. The residue was dissolved in 25 mL of diethyl ether and the ether solution was washed with 10 mL of 1N aqueous sodium hydroxide solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The product was purified by chromatography on silica gel eluted with 20% ethyl acetate in hexanes to give 0.4 g (39% yield) of the title compound as a white solid; DCI MS: 475 (M+NH4)+, 458 (M+H)+, 367 (M-benzyl+H)+, 324 (M-benzyloxy-carbonyl+2H)+. 1H NMR (CDCl3) δ:1.6-1.7 (m, 3H), 2.2-2.35 (m, 2H), 2.6-2.75 (m, 2H), 2.9-3.0 (m, 3H), 3.2-3.3 (m, 1H), 3.73 (s, 3H), 3.82 (s, 3H), 4.65-4.7 (m, 1H), 5.08 (s, 2H), 6.54 (s, 1H), 7.2-7.4 (m, 10H).

Provenance & Evidence