tert-Butyl carbamate

In a dry reaction flask, add Boc anhydride (0.8 mmol) and ethanol (3.5 mL), then cool the reaction mixture to an ice bath. Slowly add 70% ammonia solution (0.6 mL) dropwise to the reaction system. Stir the mixture at approximately 0 °C for 1 hour, then transfer the reaction mixture to room temperature and stir at room temperature for 18 hours. After the reaction is complete (monitored by TLC), heat the reaction mixture at 50 °C to evaporate the organic solvent. Dissolve the resulting residue in n-hexane (10 mL), then heat the mixture at 60 °C for 1 hour. Purify the mixture by recrystallization from the cooled n-hexane to obtain tert-butyl carbamate.

Figure: Synthetic Route of Tert-Butyl Carbamate

White to slightly yellow needles

tert-Butyl carbamate was used in palladium-catalyzed synthesis of N-Boc-protected anilines. It was used in the synthesis of tetrasubstituted pyrroles, functionalized with ester or ketone groups at C-3 position.

The Journal of Organic Chemistry, 28, p. 3421, 1963 DOI: 10.1021/jo01047a033

Palladium-catalyzed cross-coupling reaction of tert-butyl carbamate with various aryl(Het) halides with Cs₂CO₃ as base in 1,4-dioxane (solvent) has been investigated.