Burschkies, Karl published the artcileThe importance of cyclic acids and alcohols for the chemotherapy of leprosy, Application In Synthesis of 18928-94-4, the publication is Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft (1943), 328-36, database is CAplus.
New cyclopentyl derivatives are prepared and their effect on rat leprosy is examined Refluxing 23 g. Na, 130 g. AcCH2CO2Et in 500 cc. xylene, and 149 g. freshly distilled cyclopentyl bromide for 20 hrs. at 140° gives Et cyclopentaneacetoacetate (I), b12 120-2°, n20D 1.4646. Refluxing 198 g. of I with 23 g. Na in 600 cc. absolute alc. for several hrs. gives Et cyclopentaneacetate (II), b12 74-5°, n20D 1.4357. II (156 g.) in 1200 cc. absolute alc. treated with 100 g. Na gives cyclopentaneëthanol (III), b13 80-1°, n19D 1.4572. Saponification of II during the previous reaction transforms part of it into cyclopentaneacetic acid (IV) which is isolated by acidifying, shaking with Et2O, washing and drying over Na2SO4, b13 119-20°, n19D 1.4527. Treating IV with SOCl2 at 0°, heating to 70° for 1/2 hr., and distilling off the SOCl2 gives cyclopentaneacetyl chloride, b12 60°, which is reacted with hydnocarpic alc. to form hydnocarpyl cyclopentaneacetate (V), b0.02 205-10°, n20D 1.4720. Adding PBr3 to III in toluene gives 2-cyclopentylethyl bromide (VI), b. 78-9°, n20D 1.4866. After combining finely powd. Na with CH2(CO2Et)2 in xylene solution VI is added. By refluxing for 24 hrs. at 130° di-Et (2-cyclopentylethyl)malonate (VII) is formed, b13 158-60°, n22D 1.4470. By saponification of VII (2-cyclopentylethyl)malonic acid, m. 120°, and by subsequent decarboxylation at 15 mm. and 200° cyclopentanebutyric acid (VIII), b0.0-80.1 115-17°, n20D 1.4579, are formed. By heating VIII with benzyl alc. in a N atm. for 6 hrs. at 160-80°, taking up with Et2O, and shaking with 4% KOH benzyl cyclopentanebutyrate, b0.05, 138-40°, n21D 1.5248, is formed. Esterification of VIII with EtOH gives the Et ester (IX), b0.08 75°, n20D 1.4433. By reduction of IX with Na and absolute alc. cyclopentanebutanol (X), b12 109-10°, n22D 1.4610, is formed. Reacting X in toluene with freshly distilled PBr3 gives 4-cyclopentylbutyl bromide (XI), b15 107°, n22D 1.4815, which gives with CH2(CO2Et)2 and Na di-Et(4-cyclopentylbutyl)malonate (XII), b0.1 140-2°, n22D 1.4494. By saponification of XII (4-cyctopentylbutyl)malonic acid, m. 125-6°, and by further decarboxylation cyclopentanecaproic acid (XIII), b0.1 133°, m. 36-7°, are formed. By heating XIII in N for 4 hrs. with benzyl alc. to 190-200° the benzyl ester, b0.1 163°, n21D 1.5010, is obtained. Esterification of XIII with EtOH gives the Et ester, b12 136-7°, n22D 1.4462, which is reduced by Na to cyclopentanehexanol (XIV), b12 130-2°, n20D 1.4630. Esterification of III, X, XIV with PhCH:CHCOCl gives 2-cyclopentylethyl cinnamate, b0.1 188°, n20D 1.5521, 4-cyclopentylbutyl cinnamate, b0.1 190°, n21D 1.5428, 6-cyclopentylhexyl cinnamate, b0.0 190°, n20D 1.5372. The study of the therapeutic effect of cyclopentyl compounds shows that compounds with over 3 CH2-groups are effective on rat leprosy. The cyclopentyl compounds are better tolerated than the corresponding cyclopentenyl compounds The cinnamic esters of III, X, XIV show a very good therapeutic effect on rat leprosy.
Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft published new progress about 18928-94-4. 18928-94-4 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic cyclic hydrocarbon, name is (2-Bromoethyl)cyclopentane, and the molecular formula is C7H13Br, Application In Synthesis of 18928-94-4.
Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary