Ethyl Acetate → HCID 68001476, compound

Participants

Reaction Steps

A mixture of (R)-1-((S)-1-(4-(6-methoxy-2-(4-methoxyphenyl)-1H-inden-3-yl)phenoxy)propan-2-yl)-3-methylpyrrolidine (400 mg, 0.85 mmol), 10% Pd/C (350 mg, 0.33 mmol), ethyl acetate (8 mL), and ethanol (8 mL) was shaken at 65 psi of H2 for 25 h. The sides of the reaction vessel were rinsed (4 mL, 1:1 EtOAc/EtOH), and the mixture was shaken at 65 psi of H2 for an additional 22.5 h. The reaction was filtered through Celite. The Celite was washed (200 mL, 1:1 EtOAc/EtOH), and the filtrate was concentrated and purified by silica gel chromatography (1:0→17:3; dichloromethane:methanol) to give 343 mg of (3R)-1-((2S)-1-(4-(5-methoxy-2-(4-methoxyphenyl)-2,3-dihydro-1H-inden-1-yl)phenoxy)propan-2-yl)-3-methylpyrrolidine: 1H NMR (400 MHz, DMSO-d6): δ 6.99 (d, 1H), 6.92 (d, 1H), 6.80 (d, 2H), 6.74 (dd, 1H), 6.66-6.57 (m, 4H), 6.50 (d, 2H), 4.51 (d, 1H), 3.96-3.87 (m, 2H), 3.77 (s, 3H), 3.63 (s, 3H), 3.70-3.60 (br, 1H), 3.26 (dd, 1H), 3.12 (dd, 1H), 2.81 (br, 1H), 2.70-2.50 (br, 3H), 2.07 (br, 2H), 1.88 (br, 1H), 1.24 (br, 1H), 1.07 (br d, 3H), 0.96 (d, 3H); LCMS: 472.8 (M+H)+.

Provenance & Evidence