Reaction #9427

Reaction equation

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)

Solvents

methanol

Conditions

Workup

1. 1
   OtherMethanol was evaporated in vacuo
2. 2
   workup.ADDITIONEthyl acetate was added to the residue
3. 3
   Washthis mixture was washed with ammonium chloride solution
4. 4
   DryingEthyl acetate was dried over magnesium sulfate, ethyl acetate
5. 5
   Othercollected
6. 6
   Otherevaporated in vacuo
7. 7
   Otherchromatographed on alumina 90 (9:1 Hexane/EtOAc) to the desired product (6.5 g, 60%)

Procedure

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).

Source