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

HRID 1002

반응식

HRID 1002 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

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%

후처리

  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)

출처 및 근거

ORD 기록
ord-a05cf5e0c43f4ae0a2ddb5d7e074dffb
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723450

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