【结 构 式】 |
【分子编号】21515 【品名】2-methoxy-2-methyl-1-propanamine 【CA登记号】 |
【 分 子 式 】C5H13NO 【 分 子 量 】103.16436 【元素组成】C 58.21% H 12.7% N 13.58% O 15.51% |
合成路线1
该中间体在本合成路线中的序号:(III)This compound can be prepared by two different ways: 1) The dehydration of 2-amino-2-methylpropranol (I) with H2SO4 at 170-200 C gives 2,2-dimethylazirine (II), which by reaction with methanol by means of boron trifluoride - methanol complex and fractional distillation affords 2-methoxy-2-methylpropylamine (III). The reaction of (III) with formic acid in acetic anhydride yields N-(2-methoxy-2-methylpropyl)formamide (IV), which by reaction with diphosgene (trichloromethyl chloroformate) and triethylamine in dichloromethane gives 2-methoxy-2-methylpropylisonitrile (MIBI) (V). Finally, this compound or its CuBF4 complex Cu(MIBI)4BF4 is treated with 99mTcO4 (VI) and sodium dithionite or formamide sulfinic acid respectively, in ethanol - water. 2) The methylation of methyl 2-hydroxyisobutylrate (VII) with NaH - methyl iodide in DMF - THF gives methyl 2-methoxy-2-methylpropanoate (VIII), which by reaction with ammonia is converted to the corresponding amide (IX). Finally, this compound is reduced with LiAlH4 in THF yielding the amine (III), already obtained.
【1】 Bergstein, P.L.; Subramanyam, V. (E.I. Du Pont de Nemours & Co.); Ether isonitriles and radilabeled complexes thereof. AU 8666842; EP 0233368; JP 87201363 . |
【2】 Williams, S.; Okada, R.D.; Gaffney, T.; Glover, D.; Myocardial kinetics of technetium-99m-hexakis-2-methoxy-2-methylpropyl-isonitrile. Circulation 1988, 77, 491. |
【3】 Carrell, S.A.; Robinson, C.P.; Prous, J.; Castaner, J.; TECHNETIUM [(99m)Tc] SESTAMIBI < Prop INN; BAN >. Drugs Fut 1989, 14, 12, 1169. |
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) | 21513 | 2-amino-2-methyl-1-propanol;Karl Fischer;2-Amino-2-methyl-propan-1-ol;2-amino-2-methyl-1-propanol | 124-68-5 | C4H11NO | 详情 | 详情 |
(II) | 21514 | 2,2-dimethylaziridine | C4H9N | 详情 | 详情 | |
(III) | 21515 | 2-methoxy-2-methyl-1-propanamine | C5H13NO | 详情 | 详情 | |
(IV) | 21516 | 2-methoxy-2-methylpropylformamide | C6H13NO2 | 详情 | 详情 | |
(V) | 21517 | 2-Methoxy-2-methylpropyl isocyanide | C6H11NO | 详情 | 详情 | |
(VII) | 21518 | methyl 2-hydroxy-2-methylpropanoate | 2110-78-3 | C5H10O3 | 详情 | 详情 |
(VIII) | 21519 | methyl 2-methoxy-2-methylpropanoate | C6H12O3 | 详情 | 详情 | |
(IX) | 21520 | 2-methoxy-2-methylpropanamide | C5H11NO2 | 详情 | 详情 |