Reaktion #70183

Reaktionsgleichung

6-Bromo-2-(4-methoxy-benzyl)-3,4-dihydro-2H-isoquinolin-1one

2-tert-butoxy-2-oxoethylzinc chloride

→

desired product

Ausbeute 95.6%

[2-(4-Methoxy-benzyl)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-6yl]-acetic acid tert-butyl ester

Ausbeute 95.6%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture heated for 1 hour at 70° C.
2. 2
   Sonstigethe reaction to completion

Vorschrift

6-Bromo-2-(4-methoxy-benzyl)-3,4-dihydro-2H-isoquinolin-1one(1.9 g, 5.5 mmole), Q-phos (0.0632 g, 0.11 mmole) and Pd(dba)2 (0.0781 g, 0.11 mmole) in 10 ml THF were added to 2-tert-butoxy-2-oxoethylzinc chloride 15 ml (0.55 M) under argon. The reaction mixture was stirred at room temperature for 16 hours. Next a third of the initial amount of Q-phos, Pd(dba)2 and zinc enolate were added and the mixture heated for 1 hour at 70° C. to bring the reaction to completion. The desired product (2 g ; 95.6% yield) was isolated by flash chromatography using silica gel column chromatography with 10% -40% ethylacetate in hexane as eluent.

Quelle