N-tert-Butyl adamantanyl-1-yl-carbamate could be produced through the following synthetic route.

N-tert-Butyl adamantan-1-yl-carbamate (2). A flame-dried 250-mL, three-necked, round-bottomed flask equipped with a mechanical stirrer and fitted with a thermometer and a rubber septum with an argon inlet is charged with adamantane-1-carboxylic acid (1, 5.40 g, 30.0 mmol), sodium azide (3.90 g, 60.0 mmol, 2.0 equiv)), tetra-n-butyl ammonium bromide (0.870 g, 2.70 mmol. 0.09 equiv), and finally zinc triflate (0.220 g, 0.60 mmol, 0.02 equiv). The flask is then purged with argon. After 10 min, 150 mL of THF is added via a syringe and the flask is heated in an oil bath at 40 °C. Once the internal temperature has reached 40 °C, the di-tert-butyl dicarbonate (7.58 mL, 33.0 mmol, 1.1 equiv) is added. The reaction mixture is then stirred under argon at 40 °C until >95% conversion to product is observed by GC analysis. The reaction mixture is cooled to room temperature and quenched with a 50 mL portion of a 10% aqueous solution of NaNO₂. The biphasic mixture is stirred 30 min at room temperature and transferred to a 500-mL separatory funnel. The reaction flask is washed with hexanes and water and the two layers are separated. The aqueous layer is extracted twice with hexanes (2 × 40 mL) and the combined organic layers are washed successively with saturated aqueous NH₄Cl (75 mL), brine (75 mL), and then dried over Na₂SO₄ (50 g). The organic solution is filtered into a round-bottomed 250-mL flask and concentrated at 40 °C by rotary evaporation (12-14 mmHg) to afford a white solid. The 250-mL flask is then equipped with a reflux condenser and the solid dissolved in a boiling mixture (T = 75 °C) of hexanes (90 mL) and ethyl acetate (2 mL). The suspension is heated in an oil bath at reflux for 20 min, complete dissolution of the solid occurs, along with the formation of a sluggish orange oil. The clear, colorless solution is decanted away from this orange residue into a 250 mL Erlenmeyer flask fitted with a 24/40 glass joint and then concentrated at 40 °C by rotary evaporation (12-14 mmHg) then under high vacuum (< 3 mmHg) for 30 min to afford a white solid, which is recrystallized from a mixture of hexanes (< 50-60 mL), and chloroform (< 2 mL). The resulting crystalline product is collected on a fritted funnel, the filtrate is washed with 10-15 mL of cold hexanes, and excess solvent is removed under vacuum to yield 6.03 g of product. The mother liquor is concentrated at 40 °C by rotary evaporation (12-14 mmHg) then under high vacuum (< 3 mmHg), and the resulting white solid recrystallized from hexanes (< 10 mL) to yield 0.55 g of additional product after filtration as above. The solids are combined to provide 6.58 g (87%) of the title compound as a crystalline white solid. The reaction should be conducted in a well-ventilated hood.