Ammonia → HCID 58932576, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(5′-methoxy-2′-oxospiro[1,3-dioxane-2,3′-indol]-1′(2′H)-yl)propanenitrile (1.00 g, 3.47 mmol) and wet Raney Nickel (1.00 g) in 2M EtOH.NH3 (45 mL) and THF (45 mL) was hydrogenated in a Parr Hydrogenation Bottle (250 mL) at 53 lb/in H2 for 20 hr. The mixture was filtered through Celite and the filtrate was poured into a steel pressure vessel and heated at 135° C. for 66 hr. The reaction was cooled to room temperature and concentrated. The crude product was purified on Biotage KP silica gel eluting with a step gradient CH2Cl2/CH3OH/NH4OH (98.5/1/0.5 to 97/2/1) to give the title compound as a tan solid (0.26 g, 27% ). NMR (300 Mz, DMSO-d6): consistent. MS: (API-ES+) 275[M+H].

Provenance & Evidence