盐酸 → (S)-3-Methoxy-5-(2-methylpyrrolidin-1-YL)aniline

HRID 1410109笔记

反应方程式

HRID 1410109 反应方程式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[CH3:17])[CH:6]=[C:7]([N+:9]([O-])=O)[CH:8]=1.Cl>O1CCOCC1.O.[Zn]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[C:5]([N:12]2[CH2:16][CH2:15][CH2:14][C@@H:13]2[CH3:17])[CH:4]=1

参与物

6

反应物 2

HCID 313盐酸HCID 68379376(S)-1-(3-methoxy-5-nitrophenyl)-2-methylpyrrolidine

产物 1

HCID 68379440(S)-3-Methoxy-5-(2-methylpyrrolidin-1-YL)aniline收率 72%

试剂、催化剂与溶剂 3

HCID 23994Zinc催化剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 312751,4-二氧六环溶剂

实验过程

To a suspension of (S)-1-(3-methoxy-5-nitrophenyl)-2-methylpyrrolidine (430 mg, 1.82 mmol) and Zinc (1.18 g, 18.2 mmol) in dioxane (20 mL) and H2O (10 mL) was added dropwise conc. HCl (1.8 mL) at room temperature, and the mixture was stirred for 2 h. The reaction mixture was filtered and the filtrate was adjusted to pH˜8 by the addition of solid NaHCO3, and then extracted with ethyl acetate (50 mL). The organic layer was dried with Na2SO4, concentrated and the residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1) to afford (S)-3-methoxy-5-(2-methylpyrrolidin-1-yl)benzenamine (269 mg, 72%) as yellow oil. LC-MS: 207 [M+H]+, tR=1.193 min.

后处理

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was adjusted to pH˜8 by the addition of solid NaHCO3
  3. extractionextracted with ethyl acetate (50 mL)
  4. dry with materialThe organic layer was dried with Na2SO4
  5. concentrationconcentrated
  6. customthe residue was purified by column chromatography (petroleum ether:ethyl acetate=20:1)

来源与证据

ORD记录
ord-f8d915773dc9436199ac78d19d08a571
来源数据集
uspto-grants-2014_12
专利号
US08921383B2

反应笔记

加载中…