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J.Am. Chem. SOC.1983, 105, 4781-4792 4781 (t, CHI); IR (KBr) 2225 and 2220 (C=N) cm-l; mass spectrum, m/e
 

Summary: J.Am. Chem. SOC.1983, 105, 4781-4792 4781
(t, CHI); IR (KBr) 2225 and 2220 (C=N) cm-l; mass spectrum, m/e
279.082 (M'; calcd 279.083).
Anal. Calcd for CI6Hl3N3S(M, 279.365): C, 68.79; H, 4.69; N,
15.04. Found: C, 68.65; H, 4.88; N, 14.86.
Reaction of (E)-7in Toluene. A solution of (E)-7 (0.35 g, 1.3mmol)
in 10 mL of toluene was heated at 110 OC for 90 h. After removal of
the solvent under reduced pressure, the remaining solid was triturated
with methanol to yield pure 14 in a yield of 90%.
Methyl cis-2,3,10,10a-Tetrahydro-l0-(methoxycarbonyl)-l~-[l]-
benzothieno(3,2-b]pyrrolizine-3,3,~~8-d3-10-acetate-d(16a). A solution
of (E)-8(0.35 g, 1 mmol) in 10 mL of 1-butanolwas heated at 118 OC
for 15 h. After removal of the solvent under reduced pressure a 7:3
mixture of 16a and 17a, respectively, was obtained from which 16a was
isolated as a white solid by trituration with methanol: yield 48%; mp
137-139 OC (methanol); IH NMR 6 7.7-6.9 (m, 4 H, Ar H), 3.73 and
3.72 (s, 3 H, OCH3),2.77 (br s, 1 H, CHDE), 2.2-1.4 (m, 4 H, CH,);
mass spectrum, m/e 349.129 (M'; calcd 349.129).
Anal. Calcd for C18H15D4N04S(M, 349.453): C, 61.87; H + D,
6.63; N, 4.01. Found: C, 61.95; H + D, 6.53; N, 3.94.

  

Source: Apeloig, Yitzhak - Department of Chemistry, Technion, Israel Institute of Technology

 

Collections: Chemistry