HUT39452A - Process for producing n-/cyclopropyl-methyl/-6,14-endoethano-7-/1-hydroxy-1,2,2-trimethyl-propyl/-dihydro-normorphin-6-methylester - Google Patents
Process for producing n-/cyclopropyl-methyl/-6,14-endoethano-7-/1-hydroxy-1,2,2-trimethyl-propyl/-dihydro-normorphin-6-methylesterInfo
- Publication number
- HUT39452A HUT39452A HU841261A HU126184A HUT39452A HU T39452 A HUT39452 A HU T39452A HU 841261 A HU841261 A HU 841261A HU 126184 A HU126184 A HU 126184A HU T39452 A HUT39452 A HU T39452A
- Authority
- HU
- Hungary
- Prior art keywords
- endo
- hydroxy
- resulting
- trimethyl
- propyl
- Prior art date
Links
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 title 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 238000005698 Diels-Alder reaction Methods 0.000 abstract 1
- AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 abstract 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 abstract 1
- FQXXSQDCDRQNQE-UHFFFAOYSA-N markiertes Thebain Natural products COC1=CC=C2C(N(CC3)C)CC4=CC=C(OC)C5=C4C23C1O5 FQXXSQDCDRQNQE-UHFFFAOYSA-N 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 229940093932 potassium hydroxide Drugs 0.000 abstract 1
- 235000011118 potassium hydroxide Nutrition 0.000 abstract 1
- 229960001841 potassium permanganate Drugs 0.000 abstract 1
- 239000012286 potassium permanganate Substances 0.000 abstract 1
- FQXXSQDCDRQNQE-VMDGZTHMSA-N thebaine Chemical compound C([C@@H](N(CC1)C)C2=CC=C3OC)C4=CC=C(OC)C5=C4[C@@]21[C@H]3O5 FQXXSQDCDRQNQE-VMDGZTHMSA-N 0.000 abstract 1
- 229930003945 thebaine Natural products 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
N-(cyclopropyl-methyl) -6,14-endo-ethano-7-(1-hydroxy -1, 2, 2-trimethyl-propyl)-dihydro -normorphine-6-methylester is prepd. from the Diels-Alder reaction prod. of thebaine with acrolein by reacting the resulting 6, 14-endo-etheno -7-formyl-tetrahydro -thebaine with methyl-magnesium-iodide, oxidizing the resulting 6, 14-endo-etheno-(1-hydroxy -ethyl) -tetrahydro -thebain with potassium-permanganate, hydrogenating the resulting 6, 14-endo-etheno-7-acetyl -tetrahydro-thebaine on a palladium catalyst, reacting the resulting 6, 14-endo-ethano-7-acetyl -tetrahydro-thebaine with tert. -butyl-magnesium-chloride, reacting the resulting 6, 6,14-endo-ethano-7-(1-hydroxy - 1, 2, 2-trimethyl -propyl) -tetrahydro-thebaine with cyanogen-bromide, reacting the resulting N-cyano-6,14-endo-ethano -7-(1-hydroxy-1, 2, 2-trimethyl-propyl) -tetrahydro-thebaine with potassium-hydroxide at 210 deg. C, andreacting the resulting 6,14-endo-ethano-7-(1-hydroxy -1, 2, 2-trimethyl -propyl)-dihydro -normorphine-6-methylester with bromo-methyl-cyclopropane.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN259/BOM/83A IN156632B (en) | 1983-08-22 | 1983-08-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT39452A true HUT39452A (en) | 1986-09-29 |
| HU193563B HU193563B (en) | 1987-10-28 |
Family
ID=11078963
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU841261A HU193563B (en) | 1983-08-22 | 1984-03-29 | Process for producing n-/cyclopropyl-methyl/-6,14-endoethano-7-/1-hydroxy-1,2,2-trimethyl-propyl/-dihydronormorphin-6-methylester |
Country Status (4)
| Country | Link |
|---|---|
| CA (1) | CA1212108A (en) |
| HU (1) | HU193563B (en) |
| IN (1) | IN156632B (en) |
| SU (1) | SU1362734A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080125592A1 (en) | 2006-10-17 | 2008-05-29 | Penick Corporation | Process for preparing oxymorphone, naltrexone, and buprenorphine |
| CA2674915C (en) | 2006-10-17 | 2015-06-30 | Penick Corporation | Process for preparing oxymorphone |
| US8227608B2 (en) | 2008-09-30 | 2012-07-24 | Mallinckrodt Llc | Processes for increasing the yield of opiate alkaloid derivatives |
| RU2503677C1 (en) * | 2012-08-21 | 2014-01-10 | Федеральное государственное бюджетное учреждение науки Институт элементоорганических соединений им. А.Н. Несмеянова Российской академии наук (ИНЭОС РАН) | 3,6-dimethoxy-17-methyl-7alpha-(trifluoroacetyl)-4,5alpha-epoxy-6alpha, 14alpha-ethenoisomorphinane and method for production thereof |
-
1983
- 1983-08-22 IN IN259/BOM/83A patent/IN156632B/en unknown
- 1983-11-28 CA CA000442036A patent/CA1212108A/en not_active Expired
-
1984
- 1984-03-29 HU HU841261A patent/HU193563B/en not_active IP Right Cessation
- 1984-05-21 SU SU843741238A patent/SU1362734A1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| IN156632B (en) | 1985-09-21 |
| HU193563B (en) | 1987-10-28 |
| SU1362734A1 (en) | 1987-12-30 |
| CA1212108A (en) | 1986-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |