Synthesis
General procedure for the synthesis of (S)-piperidin-2-ylmethanol from L-2-piperidinic acid: BH3-DMS (62.0 mmol, 4.0 eq.) and BF3-Et2O (15.5 mmol, 1.0 eq.) were added to a solution of (2S)-piperidine-2-carboxylic acid (15.5 mmol, 1.0 eq.) in THF (50 ml) at 0 °C. The reaction mixture was refluxed for 14 hours. After completion of the reaction, the solvent was removed by concentration under reduced pressure, followed by slow dropwise addition of MeOH (40 ml) at 0 °C. Concentrated HCl (5 ml) was added to the mixture and refluxing was continued for 2 hours. The solvent was again concentrated to remove the solvent and the residue was stirred in a DCM solution of 10% isopropanol for 15 min and filtered. The filtrate was concentrated to dryness to give the white solid product (S)-piperidin-2-ylmethanol in 80% yield.
References
[1] Tetrahedron, 2013, vol. 69, # 51, p. 10876 - 10883
[2] Tetrahedron, 2013, vol. 69, # 30, p. 6129 - 6143
[3] Patent: US2010/173889, 2010, A1. Location in patent: Page/Page column 34
[4] Patent: US2009/253669, 2009, A1. Location in patent: Page/Page column 46-47
[5] Patent: US2009/264407, 2009, A1. Location in patent: Page/Page column 77
