HCID 58197756, compound → HCID 58197056, compound

Participants

Reaction Steps

To a solution of methyl 6′-bromo-1′-(((S)-2-hydroxy-1-phenylethyl)amino)-4-methoxy-1′,3′-dihydrospiro[cyclohexane-1,2′-indene]-1′-carboxylate (0.0180 g, 0.03 mmol) in CH2Cl2 (3 mL) and MeOH (1.5 mL) was added Pb(OAc)4 (0.0500 g, 0.11 mmol) at 0° C. The mixture was stirred for 2 h. After the solvents were evaporated under reduced pressure, the residue was purified by reversed-phase HPLC (SunFire™ Prep C18 OBD™ 5 μm 19×50 mm column, 10%→90% MeOH/H2O, 0.1% CF3COOH over 8 min and then 90% MeOH/H2O, 0.1% CF3COOH over 2 min, flow rate 20 mL/min) to afford 0.0136 g (94%) of methyl 1′-amino-6′-bromo-4-methoxy-1′,3′-dihydrospiro[cyclohexane-1,2′-indene]-1′-carboxylate as a TFA salt. LC-MS tR=1.11 min in 3 min chromatography, m/z 368, 370 (MH+), 351, 353, 319, 321; 1H NMR (400 MHz, CD3OD) δ 7.57-7.54 (m, 2H), 7.31 (d, J=8 Hz, 1H), 3.79 (s, 3H), 3.35 (s, 3H), 3.25-3.15 (m, 2H), 3.04 (d, J=16 Hz, 1H), 2.09-2.06 (m, 2H), 1.61-1.29 (m, 6H); 13C NMR (100 MHz, CD3OD) δ 170.36, 143.46, 140.64, 134.50, 128.89, 128.09, 121.70, 79.44, 75.22, 56.11, 54.06, 52.58, 39.97, 31.11, 29.52, 29.44, 28.88.

Provenance & Evidence