Cesium carbonate → (S)-2-(6-Methoxy-5-nitro-pyridin-2-yloxymethyl)-pyrrolidine-1-carboxylic Acid Tert-Butyl Ester

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Reaction Steps

To a mixture of Pd(OAc)2 (0.08 g, 0.34 mmol) and [1,1′]binaphthalen-2-yl-di-tert-butyl-phosphane (0.14 g, 0.34 mmol) in toluene (10 ml) was added 6-bromo-2-methoxy-3-nitropyridine(1.0 g, 4.29 mmol), Cs2CO3 (3.5 g, 10.73 mmol), and (S)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.73 g, 8.58 mmol). The mixture was stirred under nitrogen at room temperature for 24 h. After evaporation of the solvent under reduced pressure, the residue was purified by silica gel chromatography with dichloromethane/ethyl acetate/methanol (10:0:0; 9:0.5:0.5; 7:1.5:1.5; 0:5:5) as eluent to provide 0.11 g (7.5%) of the product.

Provenance & Evidence