Ammonia → 5'-Amino-1'-(3-aminopropyl)spiro[1,3-dioxane-2,3'-indol]-2'(1'H)-one

Participants

Reaction Steps

A mixture of 3-(5′-nitro-2′-oxospiro[1,3-dioxane-2,3′-indol]-1′(2′H) -yl)propanenitrile (2.12 g, 7.76 mmol) and wet Raney Nickel (2.29 g) in 2M EtOH.NH3 (95 mL) and THF (35 mL) was hydrogenated in a Parr Hydrogenation Bottle at 50 lb/in2 H2 for 17 hr. The Raney Nickel was removed by filtration through Celite and the filtrate was concentrated. The crude product was purified on Biotage KP silica gel eluting with a step gradient of CH2Cl2/CH3OH/NH4OH (95/3/2) to (85/10/5) to give the title compound as a yellow foam (1.57 g, 73% yield). NMR (300 Mz, DMSO-d6): consistent

Provenance & Evidence