Aluminium lithium hydride → Benzyl 5-(hydroxymethyl)-2,3-dihydro-1H-inden-1-ylcarbamate

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Reaction Steps

At 0° C., LiAlH4 (2.4 M, 5.2 mL, 12.5 mmol) was added gradually to a solution of methyl 1-(benzyloxycarbonylamino)-2,3-dihydro-1H-indene-5-carboxylate (3.87 g, 11.9 mmol) in anhydrous THF (50 mL). The reaction was stirred for 1.5 h before being quenched by sequentially adding of water (450 μL), of 1 N NaOH (450 μL), and water (900 μL). The mixture was stirred for 10 minutes. Sodium sulfate was added and the mixture was filtered to remove insoluble salts. The residue was washed with ethyl acetate. The combined organic filtrates were evaporated to dryness in vacuo. The off-white residue was triturated with diethyl ether to afford the title compound as an off white solid (2.53 g, 71.5%). MS (ESI): m/z [M+NH4]+ 315.0

Provenance & Evidence