Sulfamide → (R,R)-(+)-N,N'-Bis(alpha-methylbenzyl)sulfamide

Participants

Reaction Steps

In a procedure similar to the preparation of sulfamide (8b), (R)-phenethylamine (471 mg, 501 μL, 3.84mmol) was subjected to sulfamide formation conditions (SO2Cl2, Et3N, CH2Cl20° C.-RT, 8 h). Flash chromatography (SiO2, Hexanes/EtOAc) yielded 356 mg (63%) of sulfamide (8e) as a white solid. mp=96-97° C.; TLC Rf=0.37 (3:1 Hexanes/EtOAc); [α]25D=−31.2 (c=1.02, CHCl3); 1H NMR (CDCl3, 400 MHZ) δ7.27-7.21 (m, 6H), 7.17-7.14 (m, 4H), 4.74 (s, 2H), 4.43 (dq, J=12.2. 6.2 Hz, 2H), 1.46 (d, J=6.8Hz, 6H); 13C NMR (CDCl3, 100 MHZ) δ142.7, 128.6, 127.5, 126.1, 53.7, 23.6; FTIR(neat) 3312,3032,2992,2944,1603,1493,1454,1381,1320,1149,751,701 cm−1; HRMS (M+H)+ calculated for C16H21N2O2S 305.1324, found 305.1322.

Provenance & Evidence