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【结 构 式】 
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【分子编号】60232 【品名】3-nitrotricyclo[3.3.1.1~3,7~]dec-1-ylamine; 3-nitrotricyclo[3.3.1.1~3,7~]decan-1-amine 【CA登记号】 |
【 分 子 式 】C10H16N2O2 【 分 子 量 】196.24932 【元素组成】C 61.2% H 8.22% N 14.27% O 16.31% |
合成路线1
该中间体在本合成路线中的序号：(II)The reaction of adamantan-1-amine (I) with HNO3 and H2SO4 gives 3-nitroadamantan-1-amine (II), which is hydrolyzed with KOH in hot water to yield 3-hydroxyadamantan-1-amine (III). On the other hand, the reaction of chloroacetyl chloride (IV) with L-prolinamide (V) by means of K2CO3 in THF gives 1-(chloroacetyl)-L-prolinamide (VI), which is treated with trifluoroacetic anhydride in THF to yield the corresponding nitrile (VII). Finally 3-hydroxyadamantan-1-amine (III) is condensed with the 1-(chloroacetyl)-L-prolinenitrile (VII) by means of K2CO3 in dichloromethane to afford the target adamantane derivative.
| 【1】 Villhauer, E.B. (Novartis AG); N-Substd. 2-cyanopyrrolidines. EP 1137635; JP 2002531547; US 6166063; WO 0034241 . |
| 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) | 60231 | tricyclo[3.3.1.1~3,7~]dec-1-ylamine; tricyclo[3.3.1.1~3,7~]decan-1-amine | C10H17N | 详情 | 详情 | |
| (II) | 60232 | 3-nitrotricyclo[3.3.1.1~3,7~]dec-1-ylamine; 3-nitrotricyclo[3.3.1.1~3,7~]decan-1-amine | C10H16N2O2 | 详情 | 详情 | |
| (III) | 60233 | 3-aminotricyclo[3.3.1.1~3,7~]decan-1-ol | C10H17NO | 详情 | 详情 | |
| (IV) | 11296 | 2-Chloroacetyl chloride; Chloroacetic chloride | 79-04-9 | C2H2Cl2O | 详情 | 详情 |
| (V) | 36137 | (2S)-2-pyrrolidinecarboxamide;L-prolinamide | 7531-52-4 | C5H10N2O | 详情 | 详情 |
| (VI) | 60234 | 1-(2-chloroacetyl)-2-pyrrolidinecarboxamide | C7H11ClN2O2 | 详情 | 详情 | |
| (VII) | 60235 | 1-(2-chloroacetyl)-2-pyrrolidinecarbonitrile | C7H9ClN2O | 详情 | 详情 |