SE8207084D0 - PROCEDURE FOR PREPARING HEXAHYDRO-5-HYDROXY-4-HYDROXIMETHYL-2H-CYCLOPENTA (B) -FURAN-2-UNDIVATE - Google Patents
PROCEDURE FOR PREPARING HEXAHYDRO-5-HYDROXY-4-HYDROXIMETHYL-2H-CYCLOPENTA (B) -FURAN-2-UNDIVATEInfo
- Publication number
- SE8207084D0 SE8207084D0 SE8207084A SE8207084A SE8207084D0 SE 8207084 D0 SE8207084 D0 SE 8207084D0 SE 8207084 A SE8207084 A SE 8207084A SE 8207084 A SE8207084 A SE 8207084A SE 8207084 D0 SE8207084 D0 SE 8207084D0
- Authority
- SE
- Sweden
- Prior art keywords
- general formula
- group
- image
- same meaning
- lactone
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- 125000002252 acyl group Chemical group 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- VYTZWRCSPHQSFX-UHFFFAOYSA-N 5-hydroxy-4-(hydroxymethyl)-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one Chemical class O1C(=O)CC2C(CO)C(O)CC21 VYTZWRCSPHQSFX-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229910052740 iodine Chemical group 0.000 abstract 1
- 150000002596 lactones Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003180 prostaglandins Chemical class 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 238000005809 transesterification reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a process for the preparation of hexahydro-5-hydroxy-4-hydroxymethyl-2H-cyclopenta[b]furan- 2-one derivatives with the general formula I <IMAGE> where Z is a R<1>-C6H4CO group and R<1> is a hydrogen atom, a methyl group, a phenyl group and optionally a nitro group. In this process, a halohydroxyketone is reacted with an acylating agent, where the halohydroxyketone has the general formula II <IMAGE> where X is a chlorine, bromine or iodine atom, and the said acylating agent has the general formula R<2>COY, where R1 is an alkyl group with 1-3 carbon atoms and Y is a chlorine or bromine atom or an R<2>-COO group. The reaction is carried out in the presence of tertiary amines and gives an acyl derivative with the general formula III <IMAGE> where R<2> and X have the same meaning as above. The acyl derivative obtained is oxidized with a peroxy-acid to prepare the corresponding δ-lactone. This compound is treated with an alkali metal hydroxide to convert it into the corresponding γ-lactone with the general formula V <IMAGE> where R<2> has the same meaning as above. The hydroxyl group in the compound with the general formula V is protected by a Z group, where Z has the same meaning as above. This gives a diester, whose selective transesterification leads to the Corey lactone with general formula I. This synthesis can be used for the preparation of prostaglandins.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8207084A SE429862B (en) | 1982-12-10 | 1982-12-10 | Process for the preparation of hexahydro-5-hydroxy-4- hydroxymethyl-2H-cyclopenta[b]furan-2-one derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8207084A SE429862B (en) | 1982-12-10 | 1982-12-10 | Process for the preparation of hexahydro-5-hydroxy-4- hydroxymethyl-2H-cyclopenta[b]furan-2-one derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8207084D0 true SE8207084D0 (en) | 1982-12-10 |
| SE429862B SE429862B (en) | 1983-10-03 |
| SE8207084L SE8207084L (en) | 1983-10-03 |
Family
ID=20348964
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8207084A SE429862B (en) | 1982-12-10 | 1982-12-10 | Process for the preparation of hexahydro-5-hydroxy-4- hydroxymethyl-2H-cyclopenta[b]furan-2-one derivatives |
Country Status (1)
| Country | Link |
|---|---|
| SE (1) | SE429862B (en) |
-
1982
- 1982-12-10 SE SE8207084A patent/SE429862B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE429862B (en) | 1983-10-03 |
| SE8207084L (en) | 1983-10-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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