反応 #9427

反応方程式

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)

溶媒

methanol

反応条件

後処理

1. 1
   その他Methanol was evaporated in vacuo
2. 2
   workup.ADDITIONEthyl acetate was added to the residue
3. 3
   洗浄this mixture was washed with ammonium chloride solution
4. 4
   乾燥Ethyl acetate was dried over magnesium sulfate, ethyl acetate
5. 5
   その他collected
6. 6
   その他evaporated in vacuo
7. 7
   その他chromatographed on alumina 90 (9:1 Hexane/EtOAc) to the desired product (6.5 g, 60%)

実験手順

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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