Hydrochloric Acid → (S)-2-(p-toluenesulfonylamino)-1,4-butanediol

Participants

Reaction Conditions

Reaction Steps

Dimethyl N-(p-toluenesulfonyl)-L-aspartate, (2.0 g; J. M. Theobald, M. W. Williams, G. T. Young, J. Chem. Soc., 1927 (1963)) was dissolved in tetrahydrofuran (20 mL) and NaBH4 (1.5 g) and LiCl (1.5 g) added and the mixture stirred at 0° C. for 60 to 64 hours. Ten percent hydrochloric acid (10 mL) was slowly added (caution!gas evolution) and the mixture extracted with ethyl acetate (3×20 mL). The combined organic extracts were concentrated and the residue dried under vacuum to give (S)-2-(p-toluene-sulfonylamino)-1,4-butanediol, 2, as an off-white solid (1.95 g; HPLC: 97.7%).

Provenance & Evidence