Discovery of (Bromomethyl)cyclopentane

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference of 3814-30-0, A common heterocyclic compound, 3814-30-0, name is (Bromomethyl)cyclopentane, molecular formula is C6H11Br, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of ethyl 9′-hydroxy-1 0′-methyl-2′-oxo-2′,7′-dihydrospiro[cyclobutane-1 ,6′-pyrido[2, 1-a]isoquinoline]-3′-carboxylate (90 mg, 0.265 mmol)in DMF (5 ml) was added K2C03 (73.2 mg, 0.530 mmol) and (bromomethyl)cyclopentane(51.8 mg, 0.318 mmol). The mixture was heated at 90 oc for 3 hours. The mixture wascooled to room temperature and partitioned between EtOAc and H20. The organic layerwas separated and the aqueous layer was extracted 2 times with EtOAc. The combinedorganic layers were washed brine, filtered, concentrated, and the residue purified by flashedchromatography (silica gel, 0-20 % MeOH in DCM to afford ethyl 9′-(cyclopentylmethoxy)-1 0′-methyl-2′-oxo-2′, 7′-dihydrospiro[cyclobutane-1 ,6′-pyrido[2, 1-a]isoquinoline]-3’carboxylate(60 mg, 53.7% yield). LCMS (ESI) m/z: 422.4 (M + 1t.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CATALANO, John G.; DICKSON, Hamilton D.; KAZMIERSKI, Wieslaw Mieczyslaw; LEIVERS, Martin R.; WEATHERHEAD, John Gordon; (389 pag.)WO2018/154466; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary