methyl 3-sulfanylnaphthalene-2-carboxylate

反応条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of the triflate from step A (500 mg, 1.60 mmol) and tetrakistriphenylphosphine palladium(0) (0.05 equiv, 92 mg, 0.08 mmol) in dry benzene (2 mL) under nitrogen at room temperature, a solution of sodium triisopropilsilanethiolate in dry tetrahydrofuran [1.3 equiv, prepared from triisopropilsilanethi61 (396 mg, 2.08 mmol) and sodium hydride (95%, 52 mg, 2.08 mmol) in tetrahydrofuran (2 mL) as in Example 22, Step B] was added and the reaction mixture was warmed to reflux (bath temp 90° C.) for 3.5 h. The reaction mixture was cooled down to 0° C. and tetrabutylammonium fluoride (1 M solution in tetrahydrofuran, 1.5 equiv, 3.1 mL, 3.1 mmol) and glacial acetic acid (3.5 equiv, 437 mg, 0.405 mL, 7.28 mmol) were added and the reaction mixture stirred at 0° C. for 20 min. Work-up as in Example 22, Step B gave, after flash chromatography (silica gel, hexane-ethyl acetate 25:1), the desired thiol as an oil (220 mg, 70%). The product was kept under nitrogen at −18° C. the reaction mixture was warmed The reaction mixture was cooled down to 0° C. gave was kept under nitrogen at −18° C.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of decahydroisoquinoline mesylate from preparation 3 (76 mg, 0.21 mmol) in acetone (0.5 mL), potassium carbonate solid (29 mg, 0.21 mmol) was added under nitrogen, followed by addition of a solution of thiol from step B (45 mg, 0.21 mmol) in acetone (0.5 mL) under nitrogen, and the resulting yellow suspension stirred under reflux for 7 h. More potassium carbonate solid (29 mg, 0.21 mmol) and more thiol from step B (45 mg, 0.21 mmol) in acetone (0.5 mL) were added and the mixture stirred under reflux overnight. The reaction mixture was cooled down and concentrated in vacuo. Flash chromatography (silica gel, hexane-ethyl acetate 2.5:1) gave the desired product (36.5 mg, 36% yield). was added under nitrogen under reflux for 7 h the mixture stirred under reflux overnight The reaction mixture was cooled down concentrated in vacuo