1-(4-(S),5-(S)-Bis-benzyloxy-6-(R)-benzyloxymethyl-3-(R)-hydroxy-tetrahydro-pyran-2-(R)-yl)-3-(S)-(5-chloro-2-methoxy-phenyl)-3-fluoro-6-trifluoromethyl-1,3-dihydro-indol-2-one → 3-(S)-(5-Chloro-2-methoxy-phenyl)-3-fluoro-6-trifluoromethyl-1-(3-(R),4-(S),5-(S)-trihydroxy-6-(R)-hydroxymethyl-tetrahydro-pyran-2-(R)-yl)-1,3-dihydro-indol-2-one

Participants

Reaction Steps

To a round bottom flask containing 1-(4-(S),5-(S)-Bis-benzyloxy-6-(R)-benzyloxymethyl-3-(R)-hydroxy-tetrahydro-pyran-2-(R)-yl)-3-(S)-(5-chloro-2-methoxy-phenyl)-3-fluoro-6-trifluoromethyl-1,3-dihydro-indol-2-one ((S)-VIII) (0.144 g, 0.18 mmol) was added ethyl acetate (1 mL). Platinum oxide (0.020 g, 0.09 mmol) was added to the reaction mixture which was then placed under a hydrogen atmosphere. The reaction was allowed to stir at room temperature overnight. The crude reaction mixture was purified via reverse phase column chromatography (C18, 1:1 water:acetonitrile). The title product was obtained as a white solid (0.040 g, 42%). 1H NMR (MeOH-D4, 400 MHz): δ 7.73 (dd, 1H, J=1.6 Hz, 0.9 Hz), 7.52 (s, 1H), 7.39 (m, 2H), 7.30 (dd, 1H, J=5.5 Hz, 2.0 Hz), 6.94 (dd, 1H, J=7.5 Hz, 1.2 Hz), 5.43 (d, 1H, J=9.5 Hz), 4.04 (t, 1H, J=9.1 Hz), 3.95 (dd, 1H, J=10.5 Hz, 1.4 Hz), 3.75 (dd, 1H, J=6.8 Hz, 5.3 Hz), 3.57 (s, 3H), 3.53 (m, 2H); 19F NMR (MeOH-D4, 376 MHz): δ−64.6, −161.7; LRMS: 519 [M−H]−.

Provenance & Evidence