Aniline → 3-Phenylaminocyclopentanecarboxylic acid benzyl ester

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Reaction Steps

The mixture of 3-oxocyclopentanecarboxylic acid benzyl ester (150 mg), aniline (75 mg), glacial acetic acid (200 μL), and sodium triacetoxyborohydride (230 mg) in DCM (20 mL) was stirred overnight. Upon the addition of aq. potassium carbonate (1M, 30 mL), the mixture was extracted with ethyl acetate (30 ml×2). Organic layers were combined, washed with brine, and concentrated. Flash chromatography on silica (50% ethyl acetate in hexane) gave the product as an oil: MS (m+1)=282.3.

Provenance & Evidence