Ammonia → HCID 11662369, compound

Participants

Reaction Conditions

Reaction Steps

3-[5′-{[(2R)-2-(Methoxymethyl)pyrrolidin-1-yl]sulfonyl}-2′-oxospiro[1,3-dioxane-2,3′-indol]-1′(2′H)-yl]-2,2-dimethylpropanenitrile (1.00 g, 2.16 mmol), wet Raney Nickel (1.16 g) and 2M EtOH.NH3 (100 mL) was hydrogenated in a Parr Bottle (500 mL) at 56 lb/in2 H2 for 18 hours. The Raney nickel was removed by filtration through Sulka Floc. The filtrate was poured into a steel pressure vessel and was heated at 135° C. for 20 hours. The mixture was cooled to room temperature and concentrated. The crude product was purified on Biotage KP silica gel eluting with CH2Cl2/CH3OH/NH4OH (97.75/1.5/0.75) to give the title compound as a white solid. Anal: Calc'd for C22H31N3O5S+0.2M H2O: C, 58.31% ; H, 6.98% ; N, 9.27% . Found: C, 58.10; H, 6.96; N, 9.06. NMR (400 MHz, DMSO-d6): consistent. MS: (ES+) m/z 450 [M+H]. Opt. Rotation: +75.02(calculated) at 25° C. in CH2Cl2 (1% concentration) at 589 wavelength; Analytical HPLC: major component=99.3% at 254 nm; m.p.: 169-171° C.

Provenance & Evidence