3-(hydroxymethyl)cyclopentanone
3-Hydroxymethylcyclopentanone is a precursor to synthesize methyl epijasmonate. 3-Hydroxymethylcyclopentanone compounds, which are useful as intermediates in the preparation of HIV chemokine CCR-5 receptor antagonists.
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Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to
24 months(2-8C).
Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.
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The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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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).
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