Potassium sodium tartarate → HCID 72338937, compound

Participants

Reaction Conditions

Reaction Steps

Upon cooling to 0° C. by an ice-water bath, 5-cyano-5-cyclohexylmethyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 15a (1.2 g, 3.95 mmol) was dissolved in 30 mL of dichloromethane with stirring followed by dropwise addition of diisobutylaluminium hydride (11.8 mL, 11.8 mmol). The reaction mixture was reacted for 1 hour. The reaction was monitored by TLC until the disappearance of the starting materials. Then a solution of saturated aqueous potassium sodium tartrate was added. The mixture was stirred until the solution was clear and extracted with ethyl acetate (100 mL×3). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 5-cyclohexylmethyl-5-formyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 15b (0.4 g, yield 33%) as a light yellow oil.

Provenance & Evidence