HCID 11778479, compound → HCID 10357282, compound

Participants

Reaction Steps

Following the procedure of Example 11A, but replacing the (2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine with (2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-isopropylaziridine (prepared according to Example 4), and performing the flash chromatography with ethyl acetate:n-pentane (2:8) as the eluent afforded the titled compound (0.565 g, 95%): mp 52°-4° C.; [α]D20 -34.3° (c 1.2, CHCl3); IR (KBr): 2963.9, 1755.8, 1597.5, 1209.6 1102.1, 1091.4 cm-1 ; 1H NMR (CDCl3) δ0.84 (d, J=6.6 Hz 3H), 0.89 (d, J=6.8 Hz, 3H), 1.57-1.68 (m 1H), 2.45 (s, 3H), 2.68 (dd, J=7.6 Hz, 9.9 Hz, 1H), 3.45 (d, J=7.44 Hz, 1H),3.74 (s, 3H), 7.35 (d, J=8.2 Hz, 2H), 7.86 (d, J=8.3 Hz, 2H); 13C NMR (CDCl3) δ145.0, 134.0, 129.7, 128.3, 52.6, 50.8, 41.1, 26.7, 21.6, 20.5, 18.9. Anal. Calcd for C14H19 NO4S: C, 56.55; H, 6.44. Found: C, 56.36; H, 6.63.

Provenance & Evidence