Synthesis
General procedure for the synthesis of ((S)-1-((S)-1-phenylethyl)pyrrolidin-3-yl)methanol from (S)-methyl 5-oxoimino-1-((S)-1-phenylethyl)pyrrolidin-3-carboxylate: methyl 5-oxo-1-(1-phenylethyl)-pyrrolidine-3-carboxylate (10.0 g, 40.5 mmol) was dissolved in ether and slowly added to an ether slurry of lithium aluminum hydride (LAH, 2.31 g, 60.86 mmol). The reaction mixture was heated to reflux for 4 hours. Upon completion of the reaction, it was cooled to room temperature and the reaction was quenched with an ether/water mixture. The resulting solution was continued to be stirred at room temperature for 1 hour. The reaction mixture was filtered and the solid was washed with dichloromethane. The filtrate was concentrated under reduced pressure to give 7.76 g of the target product ((S)-1-((S)-1-phenylethyl)pyrrolidin-3-yl)methanol in 94% yield. Mass spectral analysis (APCI+): m/z 206 ([M+H]+).
References
[1] Patent: WO2005/49602, 2005, A1. Location in patent: Page/Page column 88; 89; 122
[2] Patent: WO2005/49605, 2005, A1. Location in patent: Page/Page column 116; 117; 150
[3] Organic and Biomolecular Chemistry, 2017, vol. 15, # 11, p. 2397 - 2402
[4] Patent: WO2007/100670, 2007, A1. Location in patent: Page/Page column 50-51
