Reaktion #66048

Reaktionsgleichung

95

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

9-bromoanthracene

tri-o-tolylphosphine

N2

→

title compound

Ausbeute 67.0%

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

Ausbeute 67.0%

Lösungsmittel

MeOH DCM

diethyl ether

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with water (5×20 mL)
2. 2
   Sonstigedried
3. 3
   Sonstigeevaporated
4. 4
   SonstigeThe crude product was purified by flash column chromatography (15% EtOAc/hexane

Vorschrift

A solution of 95 (192 mg, 0.50 mmol), 9-bromoanthracene (141 mg, 0.55 mmol), palladium acetate (6 mg, 0.025 mmol), and tri-o-tolylphosphine (15 mg, 0.05 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 (133 mg, 0.33 mmol, 67%) as an orange oil. [α]D27 +66.9 (c. 0.1, CHCl3). 1H NMR (CDCl3, 300 MHz): δ 8.48 (s, 1H, ArH10″); 8.03 (dd, J=0.9, 8.7 Hz, 2H, ArH3″ and ArH6″); 7.63 (dd, J=0.6, 9.0 Hz, 2H, ArH8″ and ArH1″); 7.45 (m, 2H, ArH4″ and ArH5″); 7.36 (m, 6H, ArH2″ and ArH7″, 4×ArH″); 5.40 (d, J=7.8 Hz, 1H, NH); 5.04 (m, 1H, H2); 3.79 (s, 3H, OCH3); 3.32 (dd, J=5.7, 13.8 Hz, 1H, H3a); 3.25 (dd, J=6.3, 13.8 Hz, 1H, H3b); 2.08 (s, 3H, COCH3). Mass Spectrum (CI, +ve) m/z 398 (100%) [MH+]. HRMS calcd for C26H23NO3 397.1678, found 397.1675.

Quelle