Hydroxylamine → 4-Cyanobenzaldehyde

Participants

Reaction Steps

tert-Butyl azetidine-3-carboxylate (3.6) may be prepared from azetidine-3-carboxylic acid (3.5) via protection of the amine (for example with the CBZ group) followed by esterification of the acid with tert-butyl alcohol in the presence of a coupling reagent (for example CDI) and then removal of the amine protecting group. (Z)-tert-butyl 1-(4-(N′-hydroxycarbamimidoyl)benzyl)azetidine-3-carboxylate (2.1) is available from the reaction of tert-butyl azetidine-3-carboxylate (3.6) with 4-formylbenzonitrile (4.2) under reducing conditions to give 4.3, which is then reacted with hydroxylamine. Alternatively, compound 4.3 may be prepared by esterification of 4.5, which is obtained from the reaction of azetidine-3-carboxylic acid (3.5) with 4-formylbenzonitrile (4.2) under reducing conditions.

Provenance & Evidence