Tetrahydrofuran → Rel-[(3r,4s)-4-phenylpiperidin-3-yl]methanol

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1.8 g of lithium aluminum hydride in 40 mL of toluene—40 mL of THF was added 6.3 g of methyl rel-(3R,4S)-6-oxo-4-phenylpiperidine-3-carboxylate at room temperature. The reaction mixture was stirred at 75° C. for 35 hours. After completion of the reaction, it was cooled to room temperature, and 1.0 mL of water, 1.0 mL of a 1 M aqueous sodium hydroxide solution, and 1.0 mL of water added thereto in this order, followed by stirring for 10 minutes. This mixture was dried over anhydrous sodium sulfate, the insolubles were removed by filtration, and the filtrate was then concentrated under reduced pressure to obtain a white solid of 4.37 g of rel-[(3R,4S)-4-phenylpiperidin-3-yl]methanol as a crude product. ESI+: 192

Provenance & Evidence