870-46-2

Synthesis Reference(s)

Journal of the American Chemical Society, 82, p. 2725, 1960 DOI: 10.1021/ja01496a018Chemical and Pharmaceutical Bulletin, 18, p. 217, 1970 DOI: 10.1248/cpb.18.217

Purification Methods

Distil it in a Claisen flask with a water or oil bath at ca 80o. After a couple of drops have distilled, the carbazate is collected as an oil which solidifies to a snow white solid. It can be crystallised with 90% recovery from a 1:1 mixture of pet ether (b 30-60o) and pet ether (b 60-70o). [Carpino et al. Org Synth Coll Vol V 166 1973, Caprino et al. Org Synth 44 20 1964, Beilstein 3 IV 175.]

General Description

Tert-Butyl carbazate is a versatile reagent used in organic synthesis, particularly for the preparation of hydrazine derivatives. It serves as a key intermediate in reductive hydrazination reactions, as demonstrated in the synthesis of 3-substituted L-fuco-azafagomines, which act as selective inhibitors of α-L-fucosidases. Additionally, it is employed as a precursor in ring-closing metathesis (RCM) reactions to generate fluorinated cyclic hydrazines, highlighting its utility in constructing biologically relevant heterocycles. Its role in these synthetic pathways underscores its importance in medicinal chemistry and the development of potential therapeutic agents.