Reaktion #167120

Reaktionsgleichung

Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-[2-(3a,6a-dihydro-thieno[3,2-b]thiophen-2-yl)-2-oxo-ethyl]ester

N-bromosuccinimide

→

title compound

Ausbeute 66.0%

Pyrrolidine-1,2-dicarboxylic acid 2-[2-(5-bromo-3a,6a-dihydro-thieno[3,2-b]thiophen-2-yl)-2-oxo-ethyl]ester 1-tert-butyl ester

Ausbeute 66.0%

Lösungsmittel

DMF

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with saturated aqueous NaHCO3 and brine
2. 2
   TrocknenThe organic layer was dried over MgSO4
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe crude residue was purified by silica column chromatography (20% to 50% EtOAc/Hex)

Vorschrift

Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-[2-(3a,6a-dihydro-thieno[3,2-b]thiophen-2-yl)-2-oxo-ethyl]ester (595 mg, 1.5 mmol) was dissolved in DMF (7.5 mL) and treated with N-bromosuccinimide (295 mg, 1.65 mmol). The reaction mixture was stirred for 4d at RT then diluted with EtOAc and washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated. The crude residue was purified by silica column chromatography (20% to 50% EtOAc/Hex) to afford the title compound (469 mg, 66%).

Quelle