p-Toluenesulfonic acid → (2S)-(-)-2-(methoxymethyl)-1-[2-(3-quinolinyl)cyclohexylideneamino]pyrrolidine

Participants

Reaction Steps

A mixture of (±)-2-(3-quinolinyl)cyclohexanone (0.5 g, 2.2 mmol), (S)-(-)-1-amino-2-(methoxymethyl)pyrrolidine (`SAMP`)(0.28 g, 2.2 mmol) and p-toluenesulphonic acid (10 mg) was refluxed in toluene (15 ml) for 2.5 hours. The toluene was removed in vacuo (40° C./14 mmHg,) to give a crude oil which was partitioned between water (20 ml) and ethyl acetate (25 ml). The aqueous layer was extracted with ethyl acetate (2×25 ml) and the combined organic extracts were dried over sodium sulphate then concentrated in vacuo to give (2S)-(+)-2-(methoxymethyl) -1-[2-(3-quinolinyl)cyclohexylideneamino]pyrrolidine and (2S)-(-)-2-(methoxymethyl)-1-[2-(3-quinolinyl)cyclohexylideneamino]pyrrolidine as a 50:50 mixture of diastereoisomers (0.69 g, 2 mmol).

Provenance & Evidence