反应详情

A solution of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (Example 2) (73 mg, 0.2 mmol) and BOC-glycine (35 mg, 0.2 mmol) in DMF (1.0 mL) at room temperature was treated with diisopropylethylamine (35 μL, 0.2 mmol) followed by HATU (84 mg, 0.22 mmol). The reaction mixture was stirred for 2 h then partitioned between EtOAc (10 mL) and a saturated aqueous NaHCO3 solution (10 mL). The organic component was isolated and further washed with brine (10 mL) then dried over MgSO4, filtered, and evaporated to an oil which was purified by silica gel flash chromatography with 40% EtOAc/hexane as eluant to afford BOC-containing coupled product as a foam (85 mg, 81%). LC/MS 7.46 min, [M+1]+ 524. The BOC-protected intermediate was dissolved in a 4 N solution of hydrogen chloride in dioxane and stirred for 2 h then evaporated to a solid which was filtered and washed with diethyl ether to afford product as a colorless solid (42 mg, 49% based on trihydrochloride salt). LC/MS 4.66 min, [M+1]+ 424.

1. customthen partitioned between EtOAc (10 mL)
2. customThe organic component was isolated
3. washfurther washed with brine (10 mL)
4. dry with materialthen dried over MgSO4
5. filtrationfiltered
6. customevaporated to an oil which
7. customwas purified by silica gel flash chromatography with 40% EtOAc/hexane as eluant
8. customto afford BOC-
9. additioncontaining
10. customLC/MS 7.46 min, [M+1]+ 524
11. stirringstirred for 2 h
12. customthen evaporated to a solid which
13. filtrationwas filtered
14. washwashed with diethyl ether
15. customto afford product as a colorless solid (42 mg, 49% based on trihydrochloride salt)
16. customLC/MS 4.66 min, [M+1]+ 424