Sodium Hydroxide → (S)-3-(tert-butyldimethylsilanyloxy)-1-(2-fluorophenyl)propylamine

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Reaction Conditions

Reaction Steps

Under inert gas, 2.80 g of lithium aluminum hydride were added in portions to a suspension of 0.97 g of (S)-3-amino-3-(2-fluorophenyl)propionic acid in 80 ml of THF, and the reaction mixture was then stirred at a temperature of 50° C. for 3 hours. 3 ml of water, 1 ml of 12 N aqueous sodium hydroxide solution and another 10 ml of water were added and the mixture was stirred for 10 minutes. The precipitate was filtered off, the filtrate was concentrated by rotary evaporation, the residue was dissolved once again in methylene chloride, and the solution was dried over MgSO4 and concentrated by rotary evaporation. For further reaction, a solution of the residue in methylene chloride was admixed with 2.22 ml of triethylamine and 1.20 g of tert-butylchlorodimethylsilane. After stirring at room temperature overnight, the reaction solution was washed with aqueous sodium hydrogencarbonate solution, dried over MgSO4 and concentrated by rotary evaporation. The crude product was purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (880 g) with a molecular weight of 283.5 g/mol (C15H26FNOSi); MS (ESI): m/e=284 (M+H+).

Provenance & Evidence