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N-Morpholinomethyl-5-lithiotetrazole: A Reagent for the One-Pot Synthesis of 5-(1-Hydroxyalkyl)tetrazoles.

An efficient, one-pot method for the preparation of 5-(1-hydroxyalkyl)tetrazoles is reported. N-Morpholinomethyl-5-lithiotetrazole, generated by the deprotonation of 4-(N-tetrazolylmethyl)morpholine with LiHMDS, undergoes addition to ketones and aldehydes (both aromatic and aliphatic) to form 5-(1-hydroxyalkyl)tetrazoles in high yield, after acidic workup. The reported protocol displays broad substrate scope and functional group tolerance, avoids the use of cyanide or azide-based reagents and provides access to sterically-congested and unsaturated tetrazoles, which are difficult to access by other means.