Benzyl succinimido carbonate → HCID 14802498, compound

Participants

Reaction Steps

40.5 g (295 mol) of (R)-2-amino-2-phenylethanol were dissolved in 385 ml of absolute DMF. 73.5 g of N-(benzyloxycarbonyloxy)succinimide (295 mmol) were added at 0° C. with stirring and the mixture was stirred at 0° C. for 1 hour. The ice bath was removed and the batch was allowed to stand at room temperature for 48 hours. The reaction solution was concentrated in vacuo and the residue was then taken up in 500 ml of ethyl acetate. The organic phase was washed twice with 10% strength aqueous citric acid solution and once with water. It was dried over anhydrous sodium sulfate and concentrated. The crystalline crude product obtained (82.3 g) was dissolved again in ethyl acetate. The organic phase was washed twice with 10% strength aqueous citric acid solution and once with water and concentrated. The residue was then recrystallized from ethyl acetate/petroleum ether. Yield: 74.6 g (93.3%).

Provenance & Evidence