3-(hydroxymethyl)cyclopentanone

US6506908[P].2003.

Process for preparing 3-hydroxymethyl-4-(aryl or heterocyclic)-cyclopentanones[Reference: WebLink]

Processes are disclosed for preparing 3-(hydroxymethyl)cyclopentanone compounds, which are useful as intermediates in the preparation of HIV chemokine CCR-5 receptor antagonists.
METHODS AND RESULTS:
A process is described in which the compounds are prepared by opening the cyclopropyl ring of a (1-alkoxycarbonyl-2-oxo)-trans-bicyclo[3.1.0]hexane compound by addition of a nucleophile to the cyclopropyl ring, and then decarboxylating the resulting 2-alkoxycarbonyl-3-(Nu-methyl)-cyclopentanone (Nu=the added nucleophilic group) via base solvolysis. Also described is a process for preparing the bicyclo[3.1.0]hexane precursors by the catalyzed cyclopropanation of a suitable alpha-diazo-beta-ketoester. The preparation of the alpha-diazo-beta-ketoesters and precursors thereto are also disclosed.

Agric.Biol.Chem.,1991, 55(4):1013-7.

Stereoselective Synthesis of Methyl Epijasmonate[Reference: WebLink]

METHODS AND RESULTS:
Methyl epijasmonate (1) was stereoselectively synthesized from 3-(hydroxymethyl)cyclopentanone(7). The intramolecular alkylation of bromoketone (8) or (9) was the key step to exclusively afford thermodynamically more stable oxahydrindanone (10) or (11). Synthesis was achieved in a 6% overall yield in 12 steps from (7).