Reaktion #970957

Reaktionsgleichung

1,1-dimethylethyl 4-[(2-cyanophenyl)amino]-1-piperidinecarboxylate

NaOH

hydrogen peroxide

hydrogen peroxide

hydrogen peroxide

→

title compound

1,1-Dimethylethyl 4-{[2-(aminocarbonyl)phenyl]amino}-1-piperidinecarboxylate

Lösungsmittel

EtOH

water

water

water

NaCl

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction stirred at 40° C. for 1.5 h
2. 2
   workup.STIRRINGstirring
3. 3
   Temperaturheating
4. 4
   workup.WAITwere continued overnight
5. 5
   Extraktionextracted with tBuOH (5 ml)
6. 6
   ExtraktionThe organic extract
7. 7
   workup.ADDITIONwas diluted with EtOAc (15 ml)
8. 8
   Trocknendried (MgSO4)
9. 9
   Einengenconcentrated
10. 10
    WaschenColumn chromatography eluting with 0-100% EtOAc/petroleum ether

Vorschrift

To a solution of 1,1-dimethylethyl 4-[(2-cyanophenyl)amino]-1-piperidinecarboxylate (D17) (355 mg, 1.18 mmol) in EtOH (6 ml) at 40° C. was added 2M NaOH solution (2.6 ml) followed by a mixture of hydrogen peroxide solution (27% w/w, 3.7 ml) in water (2.9 ml) and the reaction stirred for 2 h. Further hydrogen peroxide solution (27% w/w, 3.7 ml) in water (2.9 ml) was added and the reaction stirred at 40° C. for 1.5 h. Another portion of hydrogen peroxide solution (27% w/w, 7.4 ml) in water (5.8 ml) was added and stirring and heating were continued overnight. The reaction mixture was diluted with saturated aqueous NaCl solution (4 ml) and extracted with tBuOH (5 ml). The organic extract was diluted with EtOAc (15 ml), dried (MgSO4) and concentrated. Column chromatography eluting with 0-100% EtOAc/petroleum ether gave the title compound (150 mg). δH (CDCl3, 250 MHz) 7.96 (1H, br d), 7.40 (1H, m), 7.31 (1H, m), 6.71 (1H, d), 6.57 (1H, t), 5.80 (2H, br s), 3.93 (2H, m), 3.53 (1H, m), 3.06 (2H, m), 1.99 (2H, m), 1.50 (2H, m), 1.47 (9H, s). MS (ES): MH+ 320.

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