PL207821B1 - Method for the manufacture of S-(-)-8-methoxy-1, 2, 3, 4-tetrahydro-2-naphtol - Google Patents
Method for the manufacture of S-(-)-8-methoxy-1, 2, 3, 4-tetrahydro-2-naphtolInfo
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- PL207821B1 PL207821B1 PL382312A PL38231207A PL207821B1 PL 207821 B1 PL207821 B1 PL 207821B1 PL 382312 A PL382312 A PL 382312A PL 38231207 A PL38231207 A PL 38231207A PL 207821 B1 PL207821 B1 PL 207821B1
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- methoxy
- tetrahydro
- alcohol
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- naphtol
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- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
Przedmiotem wynalazku jest sposób wytwarzania S-(-)-8-metoksy-1,2,3,4-tetrahydro-2-naftolu, o wzorze 2 przedstawionym na rysunku.The present invention relates to a process for the preparation of S - (-) - 8-methoxy-1,2,3,4-tetrahydro-2-naphthol of the formula (2) shown in the drawing.
Związek ten może znaleźć zastosowanie w medycynie, jako chiralny substrat w syntezie 2-aminotetralin związków wykazujących wysokie aktywności wobec receptorów dopaminowych i serotoninowych. (P. Manitto, G. Speranza, D. Monti, G. Fontana, E. Panosetti; Tetrahedron; 1995, vol. 51, ss. 11531-11546).This compound may find application in medicine as a chiral substrate in the synthesis of 2-aminotetralin compounds with high activities towards dopamine and serotonin receptors. (P. Manitto, G. Speranza, D. Monti, G. Fontana, E. Panosetti; Tetrahedron; 1995, vol. 51, pp. 11531-11546).
Brak jest doniesień literaturowych na temat wytwarzania S-(-)-8-metoksy-1,2,3,4-tetrahydro-2-naftolu z 8-metoksy-3,4-dihydro-naftalen-2-onu (8-metoksy-e-tetralonu), na drodze mikrobiologicznej transformacji.There are no literature reports on the preparation of S - (-) - 8-methoxy-1,2,3,4-tetrahydro-2-naphthol from 8-methoxy-3,4-dihydro-naphthalen-2-one (8-methoxy -e-tetralone), by microbial transformation.
Znane jest otrzymywanie tego alkoholu, lecz o konfiguracji R, przy wykorzystaniu zdolności żywych kultur szczepu Saccharomyces cerevisiae do enancjoselektywnej redukcji wspomnianego substratu, z wydajnością 61% i nadmiarem enancjomerycznym 46% (P. Manitto, G. Speranza, D. Monti, G. Fontana, E. Panosetti; Tetrahedron; 1995, vol. 51, ss. 11531-11546).It is known to obtain this alcohol, but with the R configuration, using the ability of live cultures of the Saccharomyces cerevisiae strain to enantioselectively reduce the said substrate, with an efficiency of 61% and an enantiomeric excess of 46% (P. Manitto, G. Speranza, D. Monti, G. Fontana , E. Panosetti; Tetrahedron; 1995, vol. 51, pp. 11531-11546).
Istota wynalazku polega na tym, że substrat, którym jest 8-metoksy-3,4-dihydro-naftalen-2-on, o wzorze 1, redukuje się do S-(-)-8-metoksy-1,2,3,4-tetrahydro-2-naftolu, o wzorze 2, przy pomocy systemu enzymatycznego szczepu grzyba z gatunku Cheatomium sp.The essence of the invention consists in the fact that the substrate, which is 8-methoxy-3,4-dihydro-naphthalen-2-one, of formula 1, is reduced to S - (-) - 8-methoxy-1,2,3, 4-tetrahydro-2-naphthol, formula 2, using the enzyme system of the fungus strain Cheatomium sp.
Korzystne jest, gdy redukcję prowadzi się wodną kulturą szczepu, przy ciągłym mieszaniu reagentów oraz w temperaturze 288 - 308 K.It is advantageous if the reduction is carried out with an aqueous culture of the strain, with continuous mixing of the reactants and at a temperature of 288-308 K.
Postępując zgodnie z wynalazkiem, w wyniku działania układu enzymatycznego zawartego w komórkach grzyba Cheatomium sp., następuje enancjoselektywna redukcja grupy karbonylowej ketonu do hydroksylowej alkoholu o konfiguracji S. Uzyskany w ten sposób produkt wydziela się z wodnej kultury mikroorganizmu, znanym sposobem przez ekstrakcję chloroformem.By following the invention, as a result of the enzyme system contained in the cells of the Cheatomium sp. Fungus, the carbonyl group of the ketone is reduced enantioselectively to the hydroxyl alcohol of the S configuration. The product obtained in this way is separated from the water culture of the microorganism by a known method by extraction with chloroform.
Zasadniczą zaletą wynalazku jest otrzymanie S-(-)-8-metoksy-1,2,3,4-tetrahydro-2-naftolu, z nadmiarem enancjomerycznym ee > 99%, jako jedynego produktu reakcji, z wydajnością 71%, w temperaturze pokojowej i pH bliskim obojętnemu.The main advantage of the invention is the preparation of S - (-) - 8-methoxy-1,2,3,4-tetrahydro-2-naphthol with an enantiomeric excess ee> 99% as the only reaction product with a yield of 71% at room temperature and near neutral pH.
Wynalazek jest bliżej objaśniony w przykładzie wykonania.The invention is explained in more detail in an embodiment.
P r z y k ł a d. Do kolby Erlenmajera o pojemności 250 cm3, w której znajduje się 100 cm3 sterylnej pożywki zawierającej 3 g glukozy i 1 g aminobaku wprowadza się Cheatomium sp. Po pięciu dniach wzrostu dodaje się 20 mg 8-metoksy-3,4-dihydro-naftalen-2-onu, o wzorze 1, rozpuszczonego w 1 cm3 acetonu. Transformację prowadzi się przy ciągłym wstrząsaniu przez 4 doby. Następnie uzyskany roztwór transformacyjny ekstrahuje się trzykrotnie chloroformem, osusza bezwodnym siarczanem magnezu i odparowuje rozpuszczalnik. Otrzymuje się 142 mg surowego produktu, który oczyszcza się chromatograficznie, używając jako eluentu mieszaniny heksan-aceton, w stosunku 2:1. Na tej drodze otrzymuje się 71 mg S-(-)-8-metoksy-1,2,3,4-tetrahydro-2-naftolu (wydajność 71%).Example d. To the Erlenmeyer flask with a capacity of 250 cm 3, which is 100 cm 3 of sterile medium containing 3 g of glucose and 1 g aminobaku introduced Cheatomium sp. After five days of growth, was added 20 mg of 8-methoxy-3 , 4-dihydro-naphthalen-2-one, formula I, dissolved in 1 cm 3 of acetone. The transformation is carried out under continuous shaking for 4 days. The resulting transformation solution was then extracted three times with chloroform, dried with anhydrous magnesium sulfate, and the solvent was evaporated. 142 mg of crude product are obtained, which product is purified by chromatography using a 2: 1 hexane-acetone mixture as the eluent. In this way, 71 mg of S - (-) - 8-methoxy-1,2,3,4-tetrahydro-2-naphthol are obtained (71% yield).
Uzyskany produkt charakteryzuje się następującymi danymi spektralnymi:The obtained product is characterized by the following spectral data:
1H NMR (CDCI3) δ (ppm) 1,83 (dtd, 1H, J = 12,6; 9,0; 6,0 Hz, H-3eq); 2,00 (s, 1H, -OH); 2,05 (m, 1H, Wh = 27,6 Hz, H-3a); 2,60 (dd, 1H, J = 16,8; 7,2 Hz, H-1a); 2,86 (ddd, 1H, J = 16,8; 9,0; 6,0 Hz, H-4a); 2,96 (dt, 1H, J = 16,8; 6,0 Hz, H-4eq); 3,06 (dd, 1H, J = 16,8; 5,4 Hz, H-1eq); 3,84 (s, 3H, -OCH3); 4,18 (m, 1H, Wh = 24,4 Hz, H-2a); 6,71 (d, 1H, J = 8,1 Hz, H-5); 6,77 (d, 1H, J = 7,9 Hz, H-7); 7,12 (t, 1H, J = 8,0 Hz, H-6); [α]2% = -59,8 (c = 0,9; CHCI3). 1 H NMR (CDCl 3) δ (ppm) 1.83 (dtd, 1H, J = 12.6; 9.0; 6.0 Hz, H-3eq); 2.00 (s, 1H, -OH); 2.05 (m, 1H, Wh = 27.6Hz, H-3 [alpha]); 2.60 (dd, 1H, J = 16.8; 7.2Hz, H -1a); 2.86 (ddd, 1H, J = 16.8, 9.0, 6.0 Hz, H-4a); 2.96 (dt, 1H, J = 16.8; 6.0 Hz, H-4eq); 3.06 (dd, 1H, J = 16.8, 5.4Hz, H -1eq); 3.84 (s, 3H, -OCH3); 4.18 (m, 1H, Wh = 24.4Hz, H -2a); 6.71 (d, 1H, J = 8.1Hz, H-5); 6.77 (d, 1H, J = 7.9Hz, H-7); 7.12 (t, 1H, J = 8.0Hz, H-6); [α] 2 % = -59.8 (c = 0.9; CHCl3).
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL382312A PL207821B1 (en) | 2007-04-27 | 2007-04-27 | Method for the manufacture of S-(-)-8-methoxy-1, 2, 3, 4-tetrahydro-2-naphtol |
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| Application Number | Priority Date | Filing Date | Title |
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| PL382312A PL207821B1 (en) | 2007-04-27 | 2007-04-27 | Method for the manufacture of S-(-)-8-methoxy-1, 2, 3, 4-tetrahydro-2-naphtol |
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| PL382312A1 PL382312A1 (en) | 2007-10-15 |
| PL207821B1 true PL207821B1 (en) | 2011-02-28 |
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| PL382312A PL207821B1 (en) | 2007-04-27 | 2007-04-27 | Method for the manufacture of S-(-)-8-methoxy-1, 2, 3, 4-tetrahydro-2-naphtol |
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