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

HRID 1002

Reaktionsgleichung

[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

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

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%

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag: ord-a05cf5e0c43f4ae0a2ddb5d7e074dffb
Quelldatensatz: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05723450

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