N-bromobutanimide → HCID 54850283, compound

Participants

Reaction Steps

A solution of 250 mg (0.918 mmol) of 4-(4-nitro-benzenesulfonyl)-morpholine in MeOH (15 mL) was treated with 20 mg of 10% Pd/C (Degussa type E101-NE/W, Aldrich, 50% by weight water) under H2 (1 atm). The mixture was stirred at RT for 1.5 h and filtered through Celite. The filter cake was washed with MeOH, and the filtrate was concentrated in vacuo. The residue was taken up in CH2Cl2 (10 mL), cooled to 0° C., and treated with 124 mg (0.698 mmol) of NBS at that temperature for 25 min. The mixture was diluted with CH2Cl2 (15 mL) and washed with saturated aqueous NaHCO3 (1×10 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. Silica gel chromatography of the residue on a 50-g Varian MegaBond Elut SPE column with 40-50% EtOAc-hexane afforded 50.0 mg (17%) of the title compound as a pale tan solid: Mass spectrum (ESI, m/z): Calcd. for C10H13N2O3SBr, 321.0 (M+H), found 320.9/322.8.

Provenance & Evidence