Reacción #66049

Ecuación de reacción

95

Methyl (2S)-2-acetamido-3-(4-trimethylstannylphenyl)propanoate

9-bromophenanthrene

tri-o-tolylphosphine

N2

→

title compound

Rendimiento 59.7%

Methyl (2S)-2-acetamido-3-(4-[9-phenanthrenyl]phenyl)propanoate

Rendimiento 59.7%

Disolventes

MeOH DCM

diethyl ether

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with water (5×20 mL)
2. 2
   Otrodried
3. 3
   Otroevaporated
4. 4
   OtroThe crude product was purified by flash column chromatography (15% EtOAc/hexane

Procedimiento

A solution of 95 (259 mg, 0.67 mmol), 9-bromophenanthrene (190 mg, 0.74 mmol), palladium acetate (8 mg, 0.034 mmol), and tri-o-tolylphosphine (20 mg, 0.067 mmol) in DMF (2 mL) was flushed with N2 for 15 min then heated to 70° C. and allowed to stir for 16 h. The reaction was diluted with diethyl ether (20 mL) and washed with water (5×20 mL), dried and evaporated. The crude product was purified by flash column chromatography (15% EtOAc/hexane then 5% MeOH/DCM) to yield the title compound (157 mg, 0.40 mmol, 59%) as a clear oil. [α]D27 +94.6 (c. 0.1, CHCl3). 1H NMR (CDCl3, 300 MHz): δ 8.77 (d, J=9.0 Hz, 1H, ArH4″); 8.71 (d, J=8.1 Hz, 1H, ArH3″); 7.89 (m, 2H, ArH1″ and ArH10″); 7.61 (m, 5H, ArH7″, ArH6″, ArH5″, ArH2″ and ArH1″); 7.48 (d, J=8.4 Hz, 2H, ArH2′ and ArH6′); 7.26 (d, J=8.1 Hz, 2H, ArH3′ and ArH5′); 6.25 (d, J=7.5 Hz, 1H, NH); 5.00 (m, 1H, H2); 3.79 (s, 3H, OCH3); 3.30 (dd, J=5.7, 13.8 Hz, 1H, H3a); 3.20 (dd, J=6.0, 13.8 Hz, 1H, H3b); 2.05 (s, 3H, COCH3). Mass Spectrum (CI, +ve) m/z 398 (100%) [MH+]. HRMS (EI) calcd for C26H23NO3 397.1678, found 397.1680.

Fuente