Dimethylformamide → (S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-3-[(S)-1-(4-trimethylsilylethynyl-phenyl)-ethyl]-[1,3]oxazinan-2-one

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

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]+.

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