Diazomethane → methyl (+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetate

HRID 2370

Reaktionsgleichung

Reaktionsgleichung von HRID 2370
[OH:1][C@@H:2]1[CH2:6][CH2:5][C@H:4]([CH2:7][C:8]([OH:10])=[O:9])[C@@H:3]1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[N+](=[CH2:18])=[N-]>CCOCC>[OH:1][C@@H:2]1[CH2:6][CH2:5][C@H:4]([CH2:7][C:8]([O:10][CH3:18])=[O:9])[C@@H:3]1[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Komponenten

4

Edukt 2

HCID 9550DiazomethaneHCID 11171909(+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetic acid

Produkt 1

HCID 7075801methyl (+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

It is to be noted that (+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetic acid, used as starting product in this variant of the process of the invention, can also be directly methylated, for example by reacting it with an excess of diazomethane in ether solution, to provide pratically pure methyl (+)-(1R,2S,3R)-3-hydroxy-2-pentyl-1-cyclopentaneacetate, which can then be converted into (+)-cis-Hedione® via oxidation.

Quellen und Nachweise

ORD-Eintrag
ord-5330fe2873fa4dd296b870c5f2f16b19
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728866

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