Ammonia → HCID 11661117, compound

Participants

Reaction Conditions

Reaction Steps

3-[5′-{[(2S)-2-(Methoxymethyl)pyrrolidin-1-yl]sulfonyl}-2′-oxospiro[1,3-dioxane-2,3′-indol]-1′ (2′H)-yl]-2,2-dimethylpropanenitrile (1.92 g, 4.14 mmol), wet Raney Nickel (3.59 g), 2M EtOH.NH3 (175 mL) were combined in a Parr Bottle (500 mL) and hydrogenated at 52 lb/in2 H2 for 18 hours. The Raney Nickel was removed by filtration through Sulka Floc and the filter pad was washed well with 2M EtOH.NH3. The filtrate was poured into a steel pressure vessel and heated at 135° C. for 21 hours. The mixture was cooled to room temperature and the solvents were removed. The crude product was purified on Biotage KP silica gel eluting with CH2Cl2/CH3OH/NH4OH (95.5/3/1.5) to give the title compound as a white solid (1.68 g, 90% yield). Anal: Calc'd. for C22H31N3O5S : C, 58.78; H, 6.95; N, 9.35; Found: C, 58.50; H, 7.02; N, 9.22. NMR: consistent. MS; (ES+) m/z 450 [M+H]. IR: consistent. m.p.: 167-169° C. Opt. Rotation: −80.62(calculated) at 25° C. in CH2Cl2 (1% concentration), wavelength 589.

Provenance & Evidence