The general procedure for the synthesis of (S)-(1,2,3,4-tetrahydroquinoline-2-yl)methanol from ethyl 1,2,3,4-tetrahydroquinoline-2-carboxylate was as follows: at 0 °C, a tetrahydrofuran solution (5 ml/mmol) of ethyl 1,2,3,4-tetrahydroquinoline-2-carboxylate (25 mmol) was slowly added dropwise to a lithium aluminium hydroxide (2 equiv) tetrahydrofuran suspension (50 ml). The reaction mixture was stirred at 25°C for 1 hr and then warmed up to reflux to continue the reaction for 4 hr. The reaction progress was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction was quenched by slow addition of saturated sodium sulfate solution to the mixture, followed by filtration through diatomaceous earth and washing of the filter cake with ethyl acetate. After combining the filtrates, the solvents were removed by concentration under reduced pressure and the resulting crude product was purified by column chromatography (eluent ratio 3:7 ethyl acetate/hexane). The yield of the final product was 50%.
