Reacción #9427

Ecuación de reacción

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)

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroMethanol was evaporated in vacuo
2. 2
   workup.ADDITIONEthyl acetate was added to the residue
3. 3
   Lavadothis mixture was washed with ammonium chloride solution
4. 4
   SecadoEthyl acetate was dried over magnesium sulfate, ethyl acetate
5. 5
   Otrocollected
6. 6
   Otroevaporated in vacuo
7. 7
   Otrochromatographed on alumina 90 (9:1 Hexane/EtOAc) to the desired product (6.5 g, 60%)

Procedimiento

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).

Fuente