Benzyl Bromide → (3R,4R)-1-Benzyl-4-hydroxy-3-pyrrolidinemethanol

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Reaction Steps

(3R,4R)-(4-Hydroxypyrrolidin-3-yl)methanol (1.18 g) was dissolved in ethanol (25 mL) and triethylamine (1.40 mL) was added to the solution. While this mixture was cooled on a sodium chloride/ice bath, benzyl bromide (1.10 mL) was added dropwise. The mixture was then stirred at room temperature for 1 hour and was concentrated under reduced pressure. The resulting residue was purified on a silica gel column (eluant=ethyl acetate: methanol=20:1) to give 1.02 g of (3R,4R)-(1-benzyl-4-hydroxypyrrolidin-3-yl)methanol as a milky white syrup-like product.

Provenance & Evidence