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【结 构 式】 
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【分子编号】42231 【品名】(1R,5R,13R,17S)-4-(cyclopropylmethyl)-10,14,17-triethoxy-13-methyl-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10,14-tetraene; (1R,5R,13R)-4-(cyclopropylmethyl)-10,14-diethoxy-13-methyl-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10,14-tetraen-17-yl ethyl ether 【CA登记号】 |
【 分 子 式 】C27H37NO4 【 分 子 量 】439.59512 【元素组成】C 73.77% H 8.48% N 3.19% O 14.56% |
合成路线1
该中间体在本合成路线中的序号：(V)A further procedure for the preparation of (I) from naltrexone (III) has been reported. Naltrexone (III) was O-alkylated with diethyl sulfate in the presence of NaH to give (IV). Deprotonation of (IV) using the combination potassium tert-butoxide/butyllithium, followed by methylation with dimethyl sulfate, yielded the 5-methyl derivative (V). The aryl- and enol ether groups of (V) were then cleaved by means of concentrated HBr.
| 【1】 Krassing, R.; et al.; A novel method for the introduction of a 5-beta-methyl group into 4,5-alpha-epoxymorphinan-6-ones via the enol ether. Helv Chim Acta 2000, 83, 2, 380. |
| 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) | 42229 | (1R,5R,13R,17S)-4-(cyclopropylmethyl)-17-ethoxy-10-hydroxy-13-methyl-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10-trien-14-one | C23H29NO4 | 详情 | 详情 | |
| (III) | 42232 | (1S,5R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10-trien-14-one | C20H23NO4 | 详情 | 详情 | |
| (IV) | 42230 | (1S,5R,17S)-4-(cyclopropylmethyl)-10,14,17-triethoxy-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10,14-tetraene; (1S,5R)-4-(cyclopropylmethyl)-10,14-diethoxy-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10,14-tetraen-17-yl ethyl ether | C26H35NO4 | 详情 | 详情 | |
| (V) | 42231 | (1R,5R,13R,17S)-4-(cyclopropylmethyl)-10,14,17-triethoxy-13-methyl-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10,14-tetraene; (1R,5R,13R)-4-(cyclopropylmethyl)-10,14-diethoxy-13-methyl-12-oxa-4-azapentacyclo[9.6.1.0(1,13).0(5,17).0(7,18)]octadeca-7(18),8,10,14-tetraen-17-yl ethyl ether | C27H37NO4 | 详情 | 详情 |