Aluminium lithium hydride → HCID 67322682, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 0.202 g (5.32 mmol) of lithium aluminum hydride in dry tetrahydrofuran (2 mL), cooled to 0° C., is added 1.70 g (3.54 mmol) of [3′-(3-chloro-benzoylamino)-5′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]-acetic acid ethyl ester as a solution in tetrahydrofuran (6 mL). The mixture is warmed to room temperature and stirred for 1 hour then cooled in an ice bath. Excess reactants are consumed by the dropwise addition of water (0.2 mL) followed by a 15% NaOH solution (0.2 mL) and additional water (0.4 mL). The mixture is stirred at room temperature for 30 minutes then filtered through a pad of diatomaceous earth. The filter pad is washed with tetrahydrofuran and the combined filtrate is concentrated under reduced pressure. The residue is purified by flash chromatography on neutral alumina to yield 1.3 g (86%) of 3-chloro-N-[4-(2-hydroxy-ethyl)-5′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-yl]-benzamide.

Provenance & Evidence