6-氯-5-硝基烟酸甲酯 → (S)-Methyl 6-(2-(methoxycarbonyl)pyrrolidin-1-yl)-5-nitronicotinate

HRID 69578笔记

反应方程式

HRID 69578 反应方程式
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([O:8][CH3:9])=[O:7].Cl[C:11]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:12]=1>CCOC(C)=O>[CH3:9][O:8][C:6]([C@@H:2]1[CH2:3][CH2:4][CH2:5][N:1]1[C:11]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:12]=1)=[O:7]

参与物

4

反应物 2

HCID 3469616-氯-5-硝基烟酸甲酯HCID 853477METHYL L-PROLINATE

产物 1

HCID 58324504(S)-Methyl 6-(2-(methoxycarbonyl)pyrrolidin-1-yl)-5-nitronicotinate收率 94%

试剂、催化剂与溶剂 1

HCID 8857乙酸乙酯溶剂

反应条件

温度
90 °C

实验过程

(S)-Methyl pyrrolidine-2-carboxylate (6.56 g, 50.8 mmol) was added to methyl 6-chloro-5-nitronicotinate (5.00 g, 23.1 mmol) and the reaction mixture was stirred at 90° C. for 10 min (exothermic reaction). It as cooled to room temperature, diluted with EtOAc (10 mL) and purified using flash column chromatography on silica gel (20-30% EtOAc in hexanes) to afford the title compound as a yellow oil (6.70 g, 94%). [M+H] calc'd for C13H15N3O6, 310; found, 310.

后处理

  1. custom(exothermic reaction)
  2. temperatureIt as cooled to room temperature
  3. custompurified

来源与证据

ORD记录
ord-c4624cc82689407eb29e51e1a7ca835d
来源数据集
uspto-grants-2014_09
专利号
US08822470B2

反应笔记

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