ES8604952A1 - Production of methyl 10/11-bromo-14, 15-dihydro-14-beta-hydroxy-(3 alpha, 16 alpha)- eburunamenine-carboxylate compound - Google Patents
Production of methyl 10/11-bromo-14, 15-dihydro-14-beta-hydroxy-(3 alpha, 16 alpha)- eburunamenine-carboxylate compoundInfo
- Publication number
- ES8604952A1 ES8604952A1 ES548562A ES548562A ES8604952A1 ES 8604952 A1 ES8604952 A1 ES 8604952A1 ES 548562 A ES548562 A ES 548562A ES 548562 A ES548562 A ES 548562A ES 8604952 A1 ES8604952 A1 ES 8604952A1
- Authority
- ES
- Spain
- Prior art keywords
- alpha
- dihydro
- beta
- hydroxy
- bromo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- VLFDXKBCNKXRBE-YTQUADARSA-N (+)-Isoeburnamine Natural products O[C@@H]1n2c3c(c4c2[C@H]2[C@@](CC)(C1)CCC[N+]2CC4)cccc3 VLFDXKBCNKXRBE-YTQUADARSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- HONLKDDLTAZVQV-NZSAHSFTSA-N Eburnamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@H]3[C@@]4(CC)C[C@@H](O)N5C2=C1 HONLKDDLTAZVQV-NZSAHSFTSA-N 0.000 abstract 1
- -1 FeCl3.6H2O Chemical class 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 229930013930 alkaloid Natural products 0.000 abstract 1
- OZDNDGXASTWERN-UHFFFAOYSA-N apovincamine Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)C=C(C(=O)OC)N5C2=C1 OZDNDGXASTWERN-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- KXGVEGMKQFWNSR-LLQZFEROSA-N deoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 KXGVEGMKQFWNSR-LLQZFEROSA-N 0.000 abstract 1
- HONLKDDLTAZVQV-UHFFFAOYSA-N eburnamine Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)N5C2=C1 HONLKDDLTAZVQV-UHFFFAOYSA-N 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
10/11 Bromo 14,15 dihydro 14-beta hydroxy (3alpha,16alpha) eburnamine 14-carboxylic acid methyl ester of formula (I) is made by (a) reaction of a mixt. of 14,15-dihydro 14 alpha/beta -hydroxy (3alpha,16alpha) eburnamenine 14-carboxylic acid methyl ester with a soln. of bromine in a halogenated organic solvent, e.g. CHCl3, in presence of a Lewis acid, e.g. FeCl3.6H2O, as catalyst at 0 deg.C; and (b) addn. of a base to alkaline pH and extraction of the alkaloids, which are purified by conventional methods.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES548562A ES8604952A1 (en) | 1985-11-05 | 1985-11-05 | Production of methyl 10/11-bromo-14, 15-dihydro-14-beta-hydroxy-(3 alpha, 16 alpha)- eburunamenine-carboxylate compound |
| JP61263637A JPH0613513B2 (en) | 1985-11-05 | 1986-11-05 | Process for producing 10 / 11-bromo-14,15-dihydro-14β-hydroxy- (3α, 16α) -ebrunnamenin-14-carboxylic acid methyl compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES548562A ES8604952A1 (en) | 1985-11-05 | 1985-11-05 | Production of methyl 10/11-bromo-14, 15-dihydro-14-beta-hydroxy-(3 alpha, 16 alpha)- eburunamenine-carboxylate compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ES8604952A1 true ES8604952A1 (en) | 1986-03-16 |
| ES548562A0 ES548562A0 (en) | 1986-03-16 |
Family
ID=8490104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES548562A Expired ES8604952A1 (en) | 1985-11-05 | 1985-11-05 | Production of methyl 10/11-bromo-14, 15-dihydro-14-beta-hydroxy-(3 alpha, 16 alpha)- eburunamenine-carboxylate compound |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPH0613513B2 (en) |
| ES (1) | ES8604952A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0795481B2 (en) * | 1988-05-26 | 1995-10-11 | 松下電工株式会社 | Electronic component encapsulation material |
| JP2008017734A (en) * | 2006-07-11 | 2008-01-31 | Memory Secret Inc | Orally administrative composition for nutritious supplement and nutritious ingestion food for improving mental function |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2458164A1 (en) * | 1973-12-18 | 1975-06-26 | Sandoz Ag | METHOD FOR PRODUCING NEW HETEROCYCLIC COMPOUNDS |
-
1985
- 1985-11-05 ES ES548562A patent/ES8604952A1/en not_active Expired
-
1986
- 1986-11-05 JP JP61263637A patent/JPH0613513B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62142174A (en) | 1987-06-25 |
| ES548562A0 (en) | 1986-03-16 |
| JPH0613513B2 (en) | 1994-02-23 |
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