Sodium Hydroxide → HCID 18657619, compound

Participants

Reaction Steps

To a solution of 1.82 g of methyl (2S,3S,4S)-3-[4-(t-butyldimethylsilyloxy)-2-(3-pyridyl)-tetrahydrofuran-3-yl]propanoate in 25 ml of methanol is added 10 ml (0.01 mol) of 1N sodium hydroxide, the mixture is stirred at room temperature overnight, evaporated to a small volume and extracted with ethyl acetate. The aqueous layer is diluted with 20 ml of methylene chloride, the mixture is cooled to 0° C. and the pH of the aqueous layer is adjusted with stirring to 5.5 with 2N aqueous hydrochloric acid. The methylene chloride layer is dried (MgSO4) and evaporated. The residue is triturated with ethyl acetate to give (2S,3S,4S)-3-[4-(t-butyldimethylsilyloxy)-2-(3-pyridyl)tetrahydrofuran-3-yl]propanoic acid with mp 93°-94° C.

Provenance & Evidence