聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯] → 1-Tert-butyloxycarbonyl-cis-2-formyl-5-phenylpyrrolidine

HRID 1162829笔记

反应方程式

HRID 1162829 反应方程式
[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10][C@@H:9]1[C:19](N(OC)C)=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].S(=O)(=O)(O)[O-].[K+].O>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:11][CH2:10][C@@H:9]1[CH:19]=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参与物

7

反应物 4

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]HCID 516920硫酸氢钾HCID 21226445Aluminium lithium hydrideHCID 866174771-Tert-butyloxycarbonyl-cis-2-{[methoxy(methyl)amino]carbonyl}-5-phenylpyrrolidine

产物 1

HCID 541676581-Tert-butyloxycarbonyl-cis-2-formyl-5-phenylpyrrolidine

试剂、催化剂与溶剂 2

HCID 8028四氢呋喃溶剂2 次HCID 8857乙酸乙酯溶剂

反应条件

温度
0 °C

实验过程

To a cold (−78° C.) solution of 1-tert-butyloxycarbonyl-cis-2-{[methoxy(methyl)amino]carbonyl}-5-phenylpyrrolidine (1.36 g, 4.07 mmol) in THF (20 mL) under an atmosphere of nitrogen, a 1M solution of LAH in THF (4.07 mL, 4.07 mmol) was added dropwise and the mixture was stirred for 30 min. The mixture was warmed to 0° C. for 30 min and then quenched with potassium bisulfate solution in water (0.969 g, 7.12 mmol). EtOAc was added and the organic phase was separated, washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a 50:50 mixture of ethyl acetate and hexane. Collection and concentration of appropriate fractions provided 1-tert-butyloxycarbonyl-cis-2-formyl-5-phenylpyrrolidine. HPLC RT=3.47 min, 99% at 215 nm (Method A); ES MS (M+H)=276.3.

后处理

  1. customthe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. additionThe residue was subjected to column chromatography on silica gel eluting with a 50:50 mixture of ethyl acetate and hexane
  7. customCollection and concentration of appropriate fractions

来源与证据

ORD记录
ord-ee4ff0ff38904d3f83c0e766d51ee13b
来源数据集
uspto-grants-2010_10
专利号
US07820680B2

反应笔记

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