methyl (2S)-1-(2-phenylacetyl)pyrrolidine-2-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Instead of N-(3-phenylpropionyl)-proline methyl ester, (a) N-phenylacetyl-proline methyl ester (Compound No. 2), (b) N-(4-phenyl-n-butyryl)-proline methyl ester (Compound No. 6) and (c) N-(5-phenyl-n-valeryl)-proline methyl ester were used as starting compounds and treated by the procedures described above to obtain the following end compounds as oil: ##STR11## treated by the procedures to obtain the following end compounds as oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Proline methyl ester hydrochloride (3.3 g) and triethylamine (2.8 ml) were suspended in dry methylene chloride (30 ml). Under cooling, phenylacetylchloride (3.4 g) and triethylamine (3.1 ml) were simultaneously added dripwise to the suspension. Thereafter, the mixture was stirred at room temperature for 2 hours, and the reaction mixture was washed successively with water, 1N HCl, water, saturated aqueous sodium bicarbonate and brine. After drying over anhydrous magnesium sulfate, the solvent was distilled off under vacuum. The resulting crude product was purified by medium-pressure liquid column chromatography on silica gel (solvent: carbon tetrachloride) to obtain the end compound an an oil (3.7 g). Under cooling the reaction mixture was washed successively with water, 1N HCl, water, saturated aqueous sodium bicarbonate and brine After drying over anhydrous magnesium sulfate the solvent was distilled off under vacuum The resulting crude product was purified by medium-pressure liquid column chromatography on silica gel (solvent: carbon tetrachloride)