Benzaldehyde → HCID 10036538, compound

Participants

Reaction Steps

(2R,3R,4R)-2-Hydroxy-3,4-dihydroxymethylpyrrolidine hydro-chloride (compound 2) (0.265 g, 1.6 mmol) was dissolved in dry methanol (25 ml), and benzaldehyde (0.159 ml, 1.6 mmol) and sodium cyanoborohydride (0.098 g, 1.6 mmol) was added. A solution of anhydrous hydrogen chloride in diethylether (2M) was added dropwise until pH 6. The resulting mixture was stirred for 24 hours at room temperature under a nitrogen atmosphere and evaporated in vacuo. Purification of the product on silica gel (Eluent: 2-propanol/methanol (4:1)) afforded (2R,3R,4R)-1-benzyl-3,4-dihydroxy-2-hydroxymethylpyrrolidine (0.304 g, yield: 87%) as an oil.

Provenance & Evidence