تفاعل #155326

معادلة التفاعل

8-(4-methoxyphenyl)-5-propoxy-1,2,3,6-tetrahydro-6-aza-cyclopenta[a]naphthalen-9-one

sodium iodide

sodium hydride

di-tert-butyl chloromethyl phosphate

→

di-tert-butyl 8-(4-methoxyphenyl)-9-oxo-5-propoxy-1,2,3,9-tetrahydro-6-aza-cyclopenta[a]naphthalen-6-ylmethyl phosphate

المردود 40.0%

المذيبات

DMF

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture was then stirred at 40° C. for 4 hours
2. 2
   درجة الحرارةcooled
3. 3
   استخلاصthe reaction mixture was subjected to extraction
4. 4
   غسيلThe thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice
5. 5
   تجفيفdried over anhydrous sodium sulfate
6. 6
   تركيزconcentrated under reduced pressure
7. 7
   أخرىThe residue was purified
8. 8
   تركيزThe purified product was concentrated under reduced pressure

الإجراء التجريبي

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%).

المصدر