Water → Piperidin-3-yl-trityl-amine

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Reaction Steps

Add 3-(trityl-amino)-piperidin-2-one (3.56 g, 10.0 mmol) in portions to a suspension of LiAlH4 (1.00 g, 26.5 mmol) in tetrahydrofuran (25 mL). Heat the reaction to reflux under nitrogen overnight. Cool the reaction to room temperature, add 1.0 mL water, follow by adding 3.0 mL 15% NaOH and 3.0 mL water. Filter the mixture, wash with tetrahydrofuran and concentrate. Patition the material between diethyl ether and water. Add 5.0N sodium hydroxide until the aqueous layer cleared. Extract he product from the aqueous layer with diethyl ether. Dry the combined organic layers over magnesium sulfate and concentrate to give 2.91 g of the title compound as a clear oil, 85% yield. 1H NMR: consistent with structure.

Provenance & Evidence