氢化钠 → 4-[O-Benzyl-N-(3,3-dimethyl-1,5-dioxaspiro[5.5]undec-9-yl)hydroxylamino]-3-methoxy-2-methylpyridine

HRID 1002

反应方程式

HRID 1002 反应方程式
[CH2:1]([O:8][NH:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]([CH3:16])[C:11]=1[O:17][CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[CH3:23][C:24]1([CH3:46])[CH2:29][O:28][C:27]2([CH2:34][CH2:33][CH:32](OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:31][CH2:30]2)[O:26][CH2:25]1>CS(C)=O.C1COCC1>[CH2:1]([O:8][N:9]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([CH3:16])[C:11]=1[O:17][CH3:18])[CH:32]1[CH2:33][CH2:34][C:27]2([O:28][CH2:29][C:24]([CH3:23])([CH3:46])[CH2:25][O:26]2)[CH2:30][CH2:31]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参与物

7

反应物 4

HCID 24758氢化钠HCID 152793584-(O-Benzylhydroxylamino)-3-methoxy-2-methylpyridineHCID 196940293,3-Dimethyl-9-tosyloxy-1,5-dioxaspiro[5.5]undecaneHCID 178418361HCID 178418361，化合物

产物 1

HCID 196939824-[O-Benzyl-N-(3,3-dimethyl-1,5-dioxaspiro[5.5]undec-9-yl)hydroxylamino]-3-methoxy-2-methylpyridine

试剂、催化剂与溶剂 2

HCID 679二甲基亚砜溶剂HCID 8028四氢呋喃溶剂

反应条件

温度
50 °C

实验过程

7.3 g of 4-(O-benzylhydroxylamino)-3-methoxy-2-methylpyridine in 30 ml of absolute DMSO are deprotonated under N2 using 0.9 g of sodium hydride (80% strength). After evolution of hydrogen has ended, 11.7 g of 3,3-dimethyl-9-tosyloxy-1,5-dioxaspiro[5.5]undecane are added in 50 ml of absolute THF. The mixture is stirred at room temperature for 1 hour and at 50° C. for 4 hours. The THF is then distilled off in vacuo and the mixture is poured into water. After extracting with methylene chloride, the product is purified by chromatography on silica gel (ethyl acetate). 6.5 g=51%

后处理

  1. distillationThe THF is then distilled off in vacuo
  2. additionthe mixture is poured into water
  3. extractionAfter extracting with methylene chloride
  4. customthe product is purified by chromatography on silica gel (ethyl acetate)

来源与证据

ORD记录
ord-a05cf5e0c43f4ae0a2ddb5d7e074dffb
来源数据集
uspto-grants-1998_03
专利号
US05723450

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