Aniline → (2-Oxo-1-(3-phenylamino-benzyl)-azepan-3-yl]-carbamic acid tert-butyl ester

Temperatur

80 °C

In a 100 ml round bottomed flask Binap, (S)-(−)2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl, (0.210 g, 0.3375 mmol) dissolved in 15 mL toluene was stirred at 80° C. for 1 minute. To the flask cooled to room temperature under inert atmosphere Pd(OAC)2 (0.050 g, 0.225 mmol) was added and the solution was stirred at room temperature for 2 minutes. To the reaction mixture [1-(3-Iodo-benzyl)-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester (1.0 g, 2.25 mmol) dissolved in 15 mL toluene, aniline (1.047 g, 11.25 mmol) and Sodium tert-butoxide (0.259 g, 2.70 mmol) were added and the solution was stirred at 80° C. for 18 h. The reaction was cooled to room temperature, diluted with 200 mL of water, and extracted twice with 100 mL of ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated to an oil. The oil was purified on flash silica gel column using 10-30% ethyl acetate in hexanes as eluent to yield 0.562 g (61%). MS (ESI) M+H=432.5

1. additionwas added
2. stirringthe solution was stirred at room temperature for 2 minutes
3. stirringthe solution was stirred at 80° C. for 18 h
4. temperatureThe reaction was cooled to room temperature
5. extractionextracted twice with 100 mL of ethyl acetate
6. dry with materialThe organic layer was dried with anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated to an oil
9. customThe oil was purified on flash silica gel column
10. customto yield 0.562 g (61%)

ORD-Eintrag

ord-cd1d4117fe8b431f866b08b35adbdc96

Quelldatensatz

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07423033B2