反应详情

温度

0 °C

A 500 mL round bottom flask equipped with stir bar was charged with CH2Cl2 (200 mL), DIEA (28 g, 0.219 mol), and 2-Amino-1-phenyl-ethanol (10 g, 0.073 mol) and cooled to 0° C. Menthoyl chloride (14.8 g, 0.073 mol) was added drop wise over a 15 min period. Once the addition was complete the reaction was allowed to warm to ambient temperature and stirred 2 h. CH2Cl2 (100 mL) and 1N HCl (100 mL) was added to the reaction mixture and stirred for an additional 20 min. The heterogeneous mixture was transferred to a separatory funnel where the aqueous phase was separated and re-extracted with CH2Cl2 (2×100 mL). The organic phases were combined and washed with 1N HCl (8×100 mL), H2O (1×100 mL), 1N NaOH (2×100 mL), brine (100 mL), dried over MgSO4, filtered and concentrated under reduced pressure. The residue was eluted through a plug of silica gel (50% ethyl acetate/hexane for elution) provided the title compounds as colorless solid (18.8 g, 85%).

1. customA 500 mL round bottom flask equipped
2. additionOnce the addition
3. temperatureto warm to ambient temperature
4. stirringstirred 2 h
5. stirringstirred for an additional 20 min
6. customThe heterogeneous mixture was transferred to a separatory funnel
7. customwhere the aqueous phase was separated
8. extractionre-extracted with CH2Cl2 (2×100 mL)
9. washwashed with 1N HCl (8×100 mL), H2O (1×100 mL), 1N NaOH (2×100 mL), brine (100 mL)
10. dry with materialdried over MgSO4
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure
13. washThe residue was eluted through a plug of silica gel (50% ethyl acetate/hexane for elution)