反应详情

温度

90 °C

CuI (0.18 g), Pd(PPh3)2Cl2 (0.33 g), and NEt3 (2.22 mL) were added successively to a flask charged with a stir bar, trimethylsilylacetylene (1.31 mL), (S)-3-[1-(4-bromo-phenyl)-ethyl]-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one (2.00 g), and N,N-dimethylformamide (15 mL) and kept at room temperature under argon atmosphere. The flask was tightly sealed and the mixture was heated to 90° C. The mixture was stirred at 90° C. overnight and then cooled to ambient temperature. Water (80 mL) and ethyl acetate (200 mL) were added and the resulting mixture was filtered over Celite. The organic phase of the filtrate was separated and washed with brine and dried (MgSO4). The solvent was evaporated and the residue was chromatographed on silica gel (cyclohexane/ethyl acetate 3:1->0:1) to afford the title compound as an oil. Yield: 0.27 g (34% of theory); LC-MS (Method 1): tR=4.27 min; Mass spectrum (ESI+): m/z=450 [M+H]+.

1. additioncharged with a stir bar
2. customkept at room temperature under argon atmosphere
3. customThe flask was tightly sealed
4. temperaturecooled to ambient temperature
5. filtrationthe resulting mixture was filtered over Celite
6. customThe organic phase of the filtrate was separated
7. washwashed with brine
8. dry with materialdried (MgSO4)
9. customThe solvent was evaporated
10. customthe residue was chromatographed on silica gel (cyclohexane/ethyl acetate 3:1->0:1)