Sodium Bicarbonate → 1-Benzyl-3-methyl-4-piperidone

Participants

Reaction Conditions

Reaction Steps

To a cooled solution of compound 3 from step 1 (8.65 g, 34.8 mmol) in THF (100 mL) at -23° C. was added 27.8mL of 1M L-selectride (27.8 mmol). The mixture was stirred at -23° C. for 2 h. After warming to RT, the reaction mixture was added to sat. NaHCO3 and partitioned. The aqueous layer was extracted with Et2O (2×50 mL). The combined organic layers were washed with brine (50 mL), dried with MgSO4 and concentrated. The product was purified by silica gel chromatography eluting with 6:1 to 3:1 hexane-EtOAc to give 2.47 g of compound 4 and 2.75 g of recovered starting material.

Provenance & Evidence