Ammonium Hydroxide → HCID 67353972, compound

Participants

Reaction Steps

Treat a 0° C. mixture of 3-cyano-2-(4,4-difluoro-piperidin-1-yl)-propionic acid methyl ester (3.74 g, 16.1 mmol) and cobalt (II) chloride hexahydrate (1.92 g, 8.07 mmol) in THF (50 mL) and water (25 mL) portion-wise with sodium borohydride (3.05 g, 80.6 mmol) and warm to room temperature and stir for 2 days under N2. Treat the reaction with 28% ammonium hydroxide (2 mL) and filter through hyflo. Remove the solvent from the filtrate in vacuo and dilute the residue with minimal water and brine and extract three times with 3:1 chloroform:isopropanol. Dry the organic layer with Na2SO4 and remove the solvent in vacuo to afford crude product. Purify on silica with a 0 to 10% methanol in CH2Cl2 gradient to afford 1.53 g (46%) of the titled product. Rf=0.43 (9/1 CH2Cl2/methanol, I2 stain). ES MS (m/z): 205 (M+).

Provenance & Evidence