• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【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%

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:(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
Extended Information