Reaktion #598496

Reaktionsgleichung

di-tert-butyl (7-bromo-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl)imidodicarbonate

Compound 118C

di-tert-butyl (7-bromo-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl)imidodicarbonate

→

Methyl 7-[bis(tert-butoxycarbonyl)amino]-2-methyl-1-oxo-2,3-dihydro-1H-isoindole-4-carboxylate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigein MeOH (5 mL) and THF (10 mL) was evacuated
2. 2
   workup.ADDITIONrefilled with carbon monoxide (3×)
3. 3
   SonstigeThe solvent was removed in vacuo
4. 4
   Waschenwashed successively with water
5. 5
   SonstigeThe desired product was purified by column chromatography

Vorschrift

A mixture of di-tert-butyl (7-bromo-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl)imidodicarbonate (Compound 118C, 500 mg, 1.13 mmol), Pd(PPh3)4 (131 mg, 0.113 mmol), in MeOH (5 mL) and THF (10 mL) was evacuated and refilled with carbon monoxide (3×), then heated at 65° C. overnight. The solvent was removed in vacuo and the crude product was taken up in EtOAc and washed successively with water then brine. The desired product was purified by column chromatography. MS (ES+): m/z 321.28 (100) [(M-Boc)H+]; HPLC: tR=1.32 min (UPLC, Analytical).

Quelle