反应详情

A solution of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (Example 2) (73 mg, 0.2 mmol) in THF (1.5 mL) at room temperature was treated with triethylamine (42 μL, 0.3 mmol) followed by benzyloxyacetyl chloride (19 μL, 0.2 mmol). The reaction mixture was stirred for 2 h then diluted with EtOAc (2 mL) and water (2 mL). The organic phase was isolated and further washed with an additional portion of a water (2 mL) followed by a brine solution (2 mL). The organic component was dried over MgSO4, filtered, and evaporated to an oil which was purified by silica gel flash chromatography with 20% then 40% EtOAc/hexane as eluant to afford coupled product as an oil (69 mg, 67%). LC/MS 7.64 min, [M+1]+ 515. The intermediate benzyloxy ether (60 mg, 0.117 mmol) was dissolved in MeOH (20 mL), purged with a stream of nitrogen, treated with 20% Pd/C (140 mg, 50% water content), and hydrogenated under 40 psi pressure of hydrogen for 4 h. The crude reaction mixture was then purged with nitrogen, filtered, evaporated, and purified by silica gel flash chromatography with 40% then 75% EtOAc/hexane as eluant to afford product as an oil (9 mg, 18%). LC/MS 6.55 min, [M+1]+ 425.

1. customThe organic phase was isolated
2. washfurther washed with an additional portion of a water (2 mL)
3. dry with materialThe organic component was dried over MgSO4
4. filtrationfiltered
5. customevaporated to an oil which
6. customwas purified by silica gel flash chromatography with 20%
7. custom40% EtOAc/hexane as eluant to afford
8. customLC/MS 7.64 min, [M+1]+ 515
9. custompurged with a stream of nitrogen
10. additiontreated with 20% Pd/C (140 mg, 50% water content)
11. waithydrogenated under 40 psi pressure of hydrogen for 4 h
12. customThe crude reaction mixture
13. customwas then purged with nitrogen
14. filtrationfiltered
15. customevaporated
16. custompurified by silica gel flash chromatography with 40%