Aluminium lithium hydride → 2-(4-Methanesulfonyl-phenyl)-5-{5-methyl-4-[2-(2-(R)-methyl-pyrrolidin-1-yl)-ethyl]-oxazol-2-yl}-pyridine

Participants

Reaction Steps

To a stirring solution of 2-{2-[6-(4-Methanesulfonyl-phenyl)-pyridin-3-yl]-5-methyl-oxazol-4-yl}-1-(2-(R)-methyl-pyrrolidin-1-yl)-ethanone (See Intermediate 21) (1.0 mmol) in tetrahydrofuran (0.10M) in a 0° C. ice bath, slowly add 1M lithium aluminum hydride in tetrahydrofuran (2.0 mmol). Remove the ice bath and stir for four hours. After this time, perform a Fieser and Fieser work up by adding water (1 mL per gram of LAH used) followed by 5N sodium hydroxide (1 mL per gram of LAH used) and then water again (3 mL per gram of LAH used). Stir this for 18 hours and then filter the reaction through Celite®. Wash the filtrate with dichloromethane while extracting with 1N hydrochloric acid. Basify the aqueous layer with 2N sodium hydroxide and extract with dichloromethane. Concentrate the organic layer and purify via radial chromatography eluting with 2M ammonia in methanol and dichloromethane. MS (m/e): 426.2 (M+1)

Provenance & Evidence