Cl.[CH3:2][N:3]1[CH2:8][CH2:7][C:6]([CH3:12])([C:9](O)=[O:10])[CH2:5][CH2:4]1.[AlH4-].[Li+].[OH-].[Na+]>O1CCCC1.O.C(OCC)C>[CH3:2][N:3]1[CH2:8][CH2:7][C:6]([CH2:9][OH:10])([CH3:12])[CH2:5][CH2:4]1To a stirred suspension of 1,4-dimethylpiperidine-4-carboxylic acid hydrogen chloride (1.00 g, 5.17 mmol) in tetrahydrofuran (18.9 mL) was added lithium tetrahydroaluminate (1.0N solution in tetrahydrofuran, 20.7 mL, 20.7 mmol) dropwise over 5 minutes. The reaction mixture was stirred at ambient temperature for 12 hours and then diluted with water (20 mL), basified to pH ˜12 by addition of sodium hydroxide pellets, and then diluted with diethyl ether (100 mL). The organic layer was separated, dried over sodium sulfate, filtered, and concentrated in vacuo to afford the title compound as a colorless oil (543 mg, 73%). 1H NMR (400 MHz, d6-DMSO) δ 4.44 (m, 1H), 3.12 (d, J=5.4, 2H), 2.50 (m, 2H), 2.39-2.31 (m, 2H), 2.13 (s, 3H), 2.12-2.09 (m, 1H), 1.42 (m, 2H), 1.16 (m, 2H), 0.82 (s, 3H).
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