1-(Phenylmethyl) butanedioate → HCID 67133347, compound

Participants

Reaction Conditions

Reaction Steps

In a 300 mL round bottom flask, fitted with reflux condenser, 4-(benzyloxy)-4-oxobutanoic acid (1.80 g, 1 eq., of Example 1) and anhydrous tetrahydrofuran (85 mL) were added. The reaction mixture was stirred under inert atmosphere and L-borneol (1.34 g, 1 eq.) was added, followed by the addition of HOBT (1.28 g, 1.1 eq.), EDC-HCl (1.81 g, 1.1 eq.) and DMAP (1.12 g, 1.1 eq). The reaction was heated in an oil bath at 50° C. for several hours until monitoring showed a substantial amount of product formation. The reaction mixture was filtered, concentrated and extracted with MTBE versus 1N HCl. The organic layer was washed with 1N HCl and brine, dried over MgSO4 and concentrated. The crude product was purified using column chromatography to give 1.83 g of a colorless oil (62%).

Provenance & Evidence