반응 #9427

반응 방정식

5′-Bromo-2′-(methylthio)spiro[cyclohexane-1,3′-[3H]indole]

O-benzylhydroxylamine hydrochloride

→

5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime)

용매

methanol

반응 조건

후처리

1. 1
   기타Methanol was evaporated in vacuo
2. 2
   workup.ADDITIONEthyl acetate was added to the residue
3. 3
   세척this mixture was washed with ammonium chloride solution
4. 4
   건조Ethyl acetate was dried over magnesium sulfate, ethyl acetate
5. 5
   기타collected
6. 6
   기타evaporated in vacuo
7. 7
   기타chromatographed on alumina 90 (9:1 Hexane/EtOAc) to the desired product (6.5 g, 60%)

실험 절차

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).

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