Sodium Hydroxide → trans 1-Benzyl-4-(4-fluorophenyl)-3-piperidinemethanol

Participants

Reaction Conditions

Reaction Steps

Lithium aluminium hydride in THF (7.24 ml of a 1M solution) was carefully added to substantially anhydrous magnesium chloride (0.698 g), in THF (32 ml) with stirring under nitrogen keeping the temperature below 20° C. The mixture was stirred and heated to 50° C. and then a solution of (+)-1-benzyl-3-hydroxymethyl-4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine (2.15 g, preparable as described in WO96/36636) in THF (3.92 ml) and toluene (2.32 ml) was added dropwise over approximately 30 minutes. The reaction mixture was stirred and boiled under reflux for 4.0 hours. The mixture was cooled to 0-5° C. in an ice/water bath whilst sodium hydroxide solution (2.48 g, 5%w/w) was added. The suspension was filtered. The residue was washed with THF (8 ml) and the combined filtrate and washings were evaporated under reduced pressure to give a yellow oil. This oil was analysed by GLC, Chiral HPLC and 1H nmr. The title compound contained 0.24% of the desfluoro compound.

Provenance & Evidence