Réaction #155326
ord-e415676f86944507862b40899374e77f
Équation de réaction
Réactifs
Réactifs
Conditions de réaction
Traitement
- 1workup.STIRRINGthe mixture was then stirred at 40° C. for 4 hours
- 2Températurecooled
- 3Extractionthe reaction mixture was subjected to extraction
- 4LavageThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice
- 5Séchagedried over anhydrous sodium sulfate
- 6Concentrationconcentrated under reduced pressure
- 7AutreThe residue was purified
- 8ConcentrationThe purified product was concentrated under reduced pressure
Mode opératoire
To a DMF solution (10 ml) of 8-(4-methoxyphenyl)-5-propoxy-1,2,3,6-tetrahydro-6-aza-cyclopenta[a]naphthalen-9-one (400 mg, 1.15 mmol) and sodium iodide (343 mg, 2.29 mmol) was added sodium hydride (60% oil base, 74.9 mg, 1.72 mmol), and the mixture was then stirred for 10 minutes at room temperature. To the resulting mixture was added a DMF solution (20 ml) of di-tert-butyl chloromethyl phosphate (888 mg, 3.43 mmol), and the mixture was then stirred at 40° C. for 4 hours. The reaction mixture was ice-cooled, ice water was added thereto, and then the reaction mixture was subjected to extraction using ethyl acetate. The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified using medium pressure liquid chromatography (NH silica gel, n-hexane:ethyl acetate=100:0→0:100). The purified product was concentrated under reduced pressure, giving a white powder of di-tert-butyl 8-(4-methoxyphenyl)-9-oxo-5-propoxy-1,2,3,9-tetrahydro-6-aza-cyclopenta[a]naphthalen-6-ylmethyl phosphate (263 mg, yield: 40%).