Triphenylphosphine → HCID 59451538, compound

Participants

Reaction Steps

Methyl 5-{[((2R)-4-{[(1,1-dimethylethyl)oxy]carbonyl}-2-morpholinyl)methyl]oxy}-1H-indole-2-carboxylate was prepared in a similar manner as described herein from 5-hydroxy-1H-indole-2-carboxylate (0.10 g, 0.5 mmol), triphenylphosphine (0.28 g, 1.0 mmol), diethyl azodicarboxylate (0.18 g, 1.0 mmol), 1,1-dimethylethyl (2R)-2-(hydroxymethyl)-4-morpholinecarboxylate (0.23 g, 1.0 mmol) and CH2Cl2 (5 mL). The crude material was purified by Reverse-Phase HPLC (water/acetonitrile with 0.1% TFA). The desired fractions were neutralized and extracted with EtOAc. The organic extracts were combined, dried over Na2SO4, filtered and evaporated to afford the title compound (0.15 g, 73%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.76 (s, 1H), 7.30 (d, 1H), 7.08 (d, 1H), 7.00 (d, 1H), 6.89 (dd, 1H), 3.94 (d, 2H), 3.81 (s, 3H), 3.78-3.92 (m, 2H), 3.59-3.73 (m, 2H), 3.35-3.46 (m, 1H), 2.76-2.97 (m, 2H), 1.36 (s, 9H)MS: m/z 391.2 (M+1).

Provenance & Evidence