Methyl 3-[4-(azetidine-1-carbonyl)-2-chloro-phenoxy]-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate → Methyl 3-[4-(azetidine-1-carbonyl)phenoxy]-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate

Participants

Reaction Steps

Methyl 3-[4-(azetidine-1-carbonyl)-2-chloro-phenoxy]-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoate (Intermediate 17) (372 mg, 0.81 mmol) was added to a suspension of 10% palladium on carbon (37 mg, catalytic) in THF (10 mL) and ethanol (10 mL) and the resulting mixture was stirred under an atmosphere of hydrogen for 16 hours. The suspension was filtered and the filtrate evaporated under reduced pressure. The residue was dissolved in ethyl acetate (30 mL), washed with water (10 mL) and brine (10 mL), dried (MgSO4) and evaporated under reduced pressure to afford the product (309 mg, 90%). 1HNMR δ (300 MHz, CDCl3) 2.10-2.23 (m, 1H), 2.36 (quintet, 2H), 2.52-2.65 (m, 1H), 2.94 (s, 3H), 3.32-3.54 (m, 2H), 3.89 (s, 3H), 4.18-4.39 (m, 4H), 4.90 (t, 1H), 6.94 (s, 1H), 7.01 (d, 2H), 7.32 (s, 1H), 7.48 (s, 1H), 7.64 (d, 2H); m/z 425 (M+H)+

Provenance & Evidence