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【结 构 式】

【分子编号】39917

【品名】(4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-8-(1-pyrrolidinyl)-1,2,3,4,4a,4b,5,7,8,9,10,10a,10b,11,12,12a-hexadecahydronaphtho[2,1-f]quinoline

【CA登记号】

【 分 子 式 】C23H38N2

【 分 子 量 】342.5682

【元素组成】C 80.64% H 11.18% N 8.18%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VIII)

Dehydroepiandrosterone acetate (I) is converted to the lactam (II), which is hydrolyzed to the alcohol (III). Oppenauer oxidation of (III) gives the a,3-unsaturated ketone (IV). The intermediate (IV) is treated with pyrrolidine in methanol to give the enamine (V) in excellent yield. The latter, on sodium borohydride reduction affords (VI), the 3beta- configuration being assigned on the basis of similar reductions reported elsewhere. Sodium and n-pentanol reduction of (VI) leads to the diamine (VII), the methyl derivative (VIII) of which is prepared and converted into the dimethiodide (HS-310).

1 Singh, H.; Paul, D.; Steroids and related studies. Part XXV. Chandonium iodide (17alpha-Methyl-3beta-pyrrolidino-17alpha-aza-D-homoandrost-5-ene-Dimethyliodide) and other quaternary ammonium steroid analogues. J Chem Soc - Perkins Trans I 1974, 1476.
2 Schmitt, J.; et al.; Recherches sur les amino-stéroïdes. VI. Stéroïdes à restes aminés fixés en C3. Préparation par réduction au borohydrurre de sodium et au diborane des "énamines" derivées de céto-3. Bull Soc Chim France 1963, 807-815.
3 Marshall, J.A.; Johnson, W.S.; Reduction od steroidal enamines. J Org Chem 1963, 28, 421-423.
4 Arya. V.P.; Chandonium iodide. Drugs Fut 1978, 3, 11, 807.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 20083 Prasterone acetate;3b-Hydroxy-5-androstene-17-one acetate;Dehydroisoandrosterone acetate;Dehydroepiandrosterone 3-acetate;Dehydroepiandrosterone acetate;(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 853-23-6 C21H30O3 详情 详情
(II) 39912 (4aS,4bR,8S,10aR,10bS,12aS)-10a,12a-dimethyl-2-oxo-1,2,3,4,4a,4b,5,7,8,9,10,10a,10b,11,12,12a-hexadecahydronaphtho[2,1-f]quinolin-8-yl acetate C21H31NO3 详情 详情
(III) 39913 (4aS,4bR,8S,10aR,10bS,12aS)-8-hydroxy-10a,12a-dimethyl-3,4,4a,4b,5,7,8,9,10,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]quinolin-2(1H)-one C19H29NO2 详情 详情
(IV) 39914 (4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-1,3,4,4a,4b,5,6,9,10,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]quinoline-2,8-dione C19H27NO2 详情 详情
(V) 11376 Pyrrolidine 123-75-1 C4H9N 详情 详情
(VI) 39915 (4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-8-(1-pyrrolidinyl)-3,4,4a,4b,5,9,10,10a,10b,11,12,12a-dodecahydronaphtho[2,1-f]quinolin-2(1H)-one C23H34N2O 详情 详情
(VII) 39916 (4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-8-(1-pyrrolidinyl)-3,4,4a,4b,5,7,8,9,10,10a,10b,11,12,12a-tetradecahydronaphtho[2,1-f]quinolin-2(1H)-one C23H36N2O 详情 详情
(VIII) 39917 (4aS,4bR,10aR,10bS,12aS)-10a,12a-dimethyl-8-(1-pyrrolidinyl)-1,2,3,4,4a,4b,5,7,8,9,10,10a,10b,11,12,12a-hexadecahydronaphtho[2,1-f]quinoline C23H38N2 详情 详情
(IX) 39918 (4aS,4bR,10aR,10bS,12aS)-1,10a,12a-trimethyl-8-(1-pyrrolidinyl)-1,2,3,4,4a,4b,5,7,8,9,10,10a,10b,11,12,12a-hexadecahydronaphtho[2,1-f]quinoline C24H40N2 详情 详情
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