tert-Butanol → tert-butyl N-(3-methylidenecyclobutyl)carbamate

Participants

Reaction Steps

To a solution of 3-methylidenecyclobutanecarboxylic acid (132 g, 1.17 mol) and Et3N (178 g, 1.76 mol) in tert-butyl alcohol (1 L) was added dropwise DPPA (574 g, 1.41 mol) and the resulting mixture was refluxed overnight. The mixture was then quenched with water (100 mL). After removal of the tert-butyl alcohol, the residue was treated with sat. NH4Cl (500 mL), and the resulting solid precipitate was collected, washed with sat. NH4Cl and sat. NaHCO3 to give the title compound (165 g, 77% yield) as a white solid.

Provenance & Evidence