Cesium carbonate → HCID 68160022, compound

Participants

Reaction Steps

A dried round bottom flask was charged with copper(I) iodide (0.10 g, 0.53 mmol), cesium carbonate (3.58 g, 11 mmol). The flask was evacuated and backfilled with nitrogen. Under the flow of nitrogen, (S)-pyrrolidin-3-yl-methanol (0.80 g, 7.9 mmol), 3-iodothiophene (0.54 ml, 5.3 mmol), 2-(2-methyl-1-oxopropyl)cyclohexanone (0.35 ml, 2.1 mmol), and N,N-dimethylformamide (5 ml) were added. The mixture was allowed to stir under nitrogen at ambient temperature for 12 hours. The mixture was diluted with ethyl acetate, passed through a glass filter to remove the inorganic salts and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=9/1 to 1/1) to afford (S)-[1-(thiophen-3-yl)pyrrolidin-3-yl]methanol (0.41 g, 2.2 mmol, 42%) as a brown oil. In the manner as above (2)-(6), with the use of methyl (3R)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate instead of methyl (3S)-5-oxo-1-[(1R)-1-phenylethyl]pyrrolidine-3-carboxylate, (R)-[1-(thiophen-3-yl)pyrrolidin-3-yl]methanol was obtained (0.19 g, 1.0 mmol).

Provenance & Evidence