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

HRID 1002

反応式

HRID 1002 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

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%

後処理

  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)

出典と根拠

ORDレコード
ord-a05cf5e0c43f4ae0a2ddb5d7e074dffb
出典データセット
uspto-grants-1998_03
特許番号
US05723450

関連ノート

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