反应详情

To a 100 mL, 3-neck, round bottom flask were added 3-(1-methyl-piperidin-4-yl)-propan-1-ol (1.91 g, 0.012 mol), Polymer Labs (Varian) PL-TPP resin (9.83 g, 0.014 mol), N,N′,N″-tri-Boc-guanidine (4.36 g, 0.012 mol) and THF (anhydrous, 100 mL). The resultant mixture was stirred and cooled to 2° C., at which time DEAD (2.53 g, 0.014 mol) was added drop wise over 10 min. Upon completion of addition, the flask was warmed to room temperature, aged for 4 h and filtered to remove the resin bound oxide. The resultant cake was rinsed with THF (25 mL) and heptane (2×25 mL). The filtrates were combined, extracted with saturated aqueous NaHCO3 (2×25 mL), dried over anhydrous MgSO4, filtered and concentrated. The resultant residue was triturated in hot ethanol (25 mL), cooled to room temperature and filtered. The filtrate was concentrated to yield N-[3-(1-methylpiperidin-4-yl)-propyl]-N,N′,N″-tri-Boc-guanidine.

1. additionwas added drop wise over 10 min
2. additionUpon completion of addition
3. filtrationfiltered
4. customto remove the resin
5. washThe resultant cake was rinsed with THF (25 mL) and heptane (2×25 mL)
6. extractionextracted with saturated aqueous NaHCO3 (2×25 mL)
7. dry with materialdried over anhydrous MgSO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe resultant residue was triturated in hot ethanol (25 mL)
11. temperaturecooled to room temperature
12. filtrationfiltered
13. concentrationThe filtrate was concentrated