Dimethyl 1-benzylpyrrolidine-3,4-dicarboxylate → [1-Benzyl-4-(hydroxymethyl)pyrrolidin-3-yl]methanol

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Reaction Steps

To a solution of dimethyl 1-benzylpyrrolidine-3,4-dicarboxylate (0.50 g) in THF (20 mL) was added LiAlH4 (3.0 eq) at 0° C. under N2. The reaction mixture was heated to the room temperature and stirred for 24 h. The reaction was quenched with water, 10% NaOH and water in turn. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) CH2Cl2/CH3OH) to give the title compound (0.31 g, 63.79%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 222.3 (M+1).

Provenance & Evidence