Diisopropylamine → HCID 68748804, Verbindung

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of diisopropylamine (2.70 ml, 18.96 mmol) in THF (20 ml), BuLi in hexanes (11.85 ml, 18.96 mmol) was added under nitrogen at 0° C. After stirred for 0.5 hour at the same temperature, the solution was cooled to −78° C. and then a solution of benzyl 3-(biphenyl-4-yl)propanoate (5 g, 15.80 mmol) in THF (20 ml) was added. After stirred for 1.5 hour at the same temperature, tert-butyl bromoacetate (3.33 ml, 22.12 mmol) was added, and then the mixture was warmed up to 0° C. The reaction mixture was allowed to stir at 0° C. for 2 hours, and then stirred at room temperature for 14 hours. The reaction mixture was poured into 150 ml of saturated aq. NH4Cl. The product was extracted twice with EtOAc. The combined organic layer was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by flash column chromatography on silica gel (eluent: heptane/EtOAc=100:0 to 10:1) to give the 1-benzyl 4-tert-butyl 2-(biphenyl-4-ylmethyl)succinate (2.97 g); Retention time=1.00 minutes (condition G); MS (m+1)=431.2.

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