(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-3-hydroxy-10,13-dimethyl-2-(4-morpholinyl)-16-(1-pyrrolidinyl)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate -Drug Synthesis Database

【结构式】

【分子编号】13652

【品名】(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-3-hydroxy-10,13-dimethyl-2-(4-morpholinyl)-16-(1-pyrrolidinyl)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate

【CA登记号】

【分子式】C₂₉H₄₈N₂O₄

【分子量】488.7112

【元素组成】C 71.27% H 9.9% N 5.73% O 13.1%

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：(VI)

The condensation of (2alpha,3alpha,5alpha,16alpha,17alpha)-2,3:16,17-diepoxyandrostan-17-ol acetate (I) with pyrrolidine (II) by means of NaOH in methanol, followed by reduction with NaBH4 in the same solvent gives (2alpha,3alpha,5alpha,16beta,17beta)-2,3-epoxy-16-(1-pyrrolidinyl) androstan-17-ol (III), which is further condensed with morpholine (IV) in refluxing water yielding (2beta,3alpha,5alpha,16beta,17beta)-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane-3,17-diol (V). Partial acetylation of (V) with acetyl chloride in dichloromethane at room temperature affords the corresponding 17-acetoxy derivative (VI), which is finally quaternized with allyl bromide (VII) in dichloromethane.

参考文献中间体

合成目标

【1】 Savage, D.S.; Sleig, T.; Carlyle, I.G. (Akzo Nobel N.V.); Novel 2beta-morpholino-androstane derivs. and process for their preparation. AU 8814570; EP 0287150; JP 1988277693; US 4894369 .
【2】 Pento, J.T.; Castaner, J.; Rocuronium Bromide. Drugs Fut 1994, 19, 9, 841.

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)	13647	(1aR,2aS,2bS,4aS,5aR,6aS,6bR,8aS,9aS)-2a,4a-dimethylhexadecahydro-4bH-oxireno[2'',3'':4',5']cyclopenta[1',2':7,8]phenanthro[2,3-b]oxiren-4-yl acetate		C₂₁H₃₀O₄	详情	详情
(II)	11376	Pyrrolidine	123-75-1	C₄H₉N	详情	详情
(III)	13649	(1R,2S,3aS,3bR,5aS,6aS,7aR,8aS,8bS,10aS)-8a,10a-Dimethyl-2-(1-pyrrolidinyl)hexadecahydro-1H-cyclopenta[7,8]phenanthro[2,3-b]oxiren-1-ol		C₂₃H₃₇NO₂	详情	详情
(IV)	10388	Morpholine	110-91-8	C₄H₉NO	详情	详情
(V)	13651	(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-10,13-Dimethyl-2-(4-morpholinyl)-16-(1-pyrrolidinyl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol		C₂₇H₄₆N₂O₃	详情	详情
(VI)	13652	(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-3-hydroxy-10,13-dimethyl-2-(4-morpholinyl)-16-(1-pyrrolidinyl)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate		C₂₉H₄₈N₂O₄	详情	详情
(VII)	11463	3-Bromo-1-propene; 3-Bromopropene；allyl bromide	106-95-6	C₃H₅Br	详情	详情

Extended Information