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【结 构 式】 
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【分子编号】69243 【品名】(R)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methylbenzenesulfonate 【CA登记号】 |
【 分 子 式 】C14H20O6S 【 分 子 量 】316.375 【元素组成】C 53.15% H 6.37% O 30.34% S 10.13% |
合成路线1
该中间体在本合成路线中的序号：(L)Treatment of the known diol (XLIX) with tosyl chloride in cold pyridine gives the primary tosylate (L), which is reacted with NaN3 in DMF to give azidoalcohol (LI). Subsequent alkylation of the secondary alcohol (LI) with MeI and NaH followed by acidic ketal hydrolysis of the resulting methyl ether (LII) affords the diol (LIII), which is converted to ditosylate (LIV) using p-TsCl and Et3N. Reduction of azide (LIV) using PPh3 in refluxing MeOH occurs with concomitant cyclization to give the pyrrolidine (LV), which is then protected as the N-Boc derivative (LVI) under standard conditions. The remaining tosylate group of (LVI) is then displaced with NaN3 in DMF to furnish azide (LVII). After reduction by catalytic hydrogenation over Pd/C, the obtained amine (LVIII) is finally protected with Boc2O and Et3N in CH2Cl2 .
| 【1】 Kumar, A.R., Reddy, J.S., Rao, B.V. A short, simple and general approach for the synthesis of (3S,4S)-3-methoxy-4-methylamino pyrrolidine and (3S,4R)-3-methoxy-4-methylamino pyrrolidine. Tetrahedron Lett 2003, 44(30): 5687-9. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXXVIII) | 69233 | (3S,4S)-tert-butyl 3-((tert-butoxycarbonyl)amino)-4-methoxypyrrolidine-1-carboxylate | C15H28N2O5 | 详情 | 详情 | |
| (XLIX) | 69242 | (R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol | C7H14O4 | 详情 | 详情 | |
| (L) | 69243 | (R)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methylbenzenesulfonate | C14H20O6S | 详情 | 详情 | |
| (LI) | 69244 | (R)-2-azido-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol | C7H13N3O3 | 详情 | 详情 | |
| (LII) | 69245 | (R)-4-((S)-2-azido-1-methoxyethyl)-2,2-dimethyl-1,3-dioxolane | C8H15N3O3 | 详情 | 详情 | |
| (LIII) | 69246 | (2S,3R)-4-azido-3-methoxybutane-1,2-diol | C5H11N3O3 | 详情 | 详情 | |
| (LIV) | 69247 | (2S,3R)-4-azido-3-methoxybutane-1,2-diyl bis(4-methylbenzenesulfonate) | C19H23N3O7S2 | 详情 | 详情 | |
| (LV) | 69248 | (3S,4R)-4-methoxypyrrolidin-3-yl 4-methylbenzenesulfonate | C12H17NO4S | 详情 | 详情 | |
| (LVI) | 69249 | (3S,4R)-tert-butyl 3-methoxy-4-(tosyloxy)pyrrolidine-1-carboxylate | C17H25NO6S | 详情 | 详情 | |
| (LVII) | 69250 | (3S,4S)-tert-butyl 3-azido-4-methoxypyrrolidine-1-carboxylate | 429673-78-9 | C10H18N4O3 | 详情 | 详情 |
| (LVIII) | 69251 | trans-3-Amino-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester;(3S,4S)-tert-butyl 3-amino-4-methoxypyrrolidine-1-carboxylate | 429673-79-0 | C10H20N2O3 | 详情 | 详情 |