Hydrochloric Acid → (3S,5R)-5-Hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol

Participants

Reaction Steps

To an ice-cold solution of 4-acetoxy-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid ethyl ester (3) (0.65 g, 1.83 mmol) in THF (10 mL) is added LiAlH4 (0.135 g, 3.66 mmol) portion wise. Then the reaction mixture is stirred at room temperature for 1 h. After completion of the reaction, it is cooled to 0° C. and then pH of reaction mixture is adjusted to 3 by adding 6N HCl (0.65 mL). The mixture is concentrated, and the residue is triturated with water (8 mL), the solid precipitated out is filtered, washed with cold water (2×4 mL), and dried under reduced pressure to give compound (4) as white solid.

Provenance & Evidence