Benzyloxyamine hydrochloride → HCID 178419047, Verbindung

HRID 277001

Reaktionsgleichung

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]=[C:6](SC)[C:5]12[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.Cl.[CH2:19]([O:26][NH2:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO>[CH2:19]([O:26][N:27]=[C:6]1[C:5]2([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=2)[NH:7]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

Reaktionsbedingungen

Temperatur: 45 °C

Versuchsvorschrift

5′-Bromo-2′-(methylthio)spiro[cyclohexane-1,3′-[3H]indole] (9.0 g, 28.98 mmol) and O-benzylhydroxylamine hydrochloride (13.8 g, 86.9 mmol) were combined in methanol (150 mL) and heated to 45° C. for 6 hours. Methanol was evaporated in vacuo. Ethyl acetate was added to the residue and this mixture was washed with ammonium chloride solution. Ethyl acetate was dried over magnesium sulfate, ethyl acetate collected evaporated in vacuo and the residue was flash chromatographed on alumina 90 (9:1 Hexane/EtOAc) to the desired product (6.5 g, 60%). 1H NMR (DMSO-d6, 300 MHz) δ 1.38-1.70 (m, 8H), 1.92-2.06 (m, 2H), 5.06 (s, 2H), 6.71 (d, 1H, J=8.26 Hz), 7.22-7.43 (m, 7H), 9.62 (s, 1H).

Aufarbeitung

customMethanol was evaporated in vacuo
additionEthyl acetate was added to the residue
washthis mixture was washed with ammonium chloride solution
dry with materialEthyl acetate was dried over magnesium sulfate, ethyl acetate
customcollected
customevaporated in vacuo
customchromatographed on alumina 90 (9:1 Hexane/EtOAc) to the desired product (6.5 g, 60%)

Quellen und Nachweise

ORD-Eintrag: ord-e9cebc96061443debf3b03d4c369ac60
Quelldatensatz: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06355648B1

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