반응 #93358

반응 방정식

DL-tryptophan methyl ester hydrochloride

n-valeraldehyde

→

methyl (1RS, 3RS)-cis-1-butyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate hydrochloride

수율 53.0%

용매

methanol

반응 조건

후처리

1. 1
   온도is refluxed for 48 hours
2. 2
   농축concentrated to about 1/5 volume
3. 3
   온도After cooling
4. 4
   기타the precipitates are separated by filtration
5. 5
   기타recrystallized from methanol

실험 절차

A mixture of DL-tryptophan methyl ester hydrochloride (30.49 g), n-valeraldehyde (12.4 g) and methanol (400 ml) is refluxed for 48 hours and then concentrated to about 1/5 volume. After cooling, the precipitates are separated by filtration and recrystallized from methanol to give methyl (1RS, 3RS)-cis-1-butyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylate hydrochloride (20.5 g, 53%), m.p. 218° C. (decomp.) The hydrochloride thus obtained is treated with aqueous ammonia and recrystallized from diisopropyl ether-isopropanol to give the corresponding free base, m.p. 85°-87° C.

출처