4-tert-Butylcyclohexanone → tert-butyl N-[(4-tert-butylcyclohexylidene)amino]carbamate

Participants

Reaction Steps

To a solution of 4-tert-butylcyclohexanone (3.95 g, 25.6 mmol) in CH2Cl2 (50 mL) was added tert-butyl hydrazinecarboxylate (3.83 g, 25.6 mmol). A 1:1 mixture of MgSO4/Na2SO4 was added to the reaction to make a slurry and the reaction was stirred vigorously. After 18 h, the reaction was diluted with CH3CN and filtered. The solvent was removed from the filtrate under reduced pressure to give 6.78 g of N′-(4-tert-butyl-cyclohexylidene)-hydrazinecarboxylic acid tert-butyl ester as a white foam. This material was used without further purification in the next step. 1H NMR (400 MHz, DMSO-d6) δ 9.51 (s, 1H), 2.93 (d, J=15 Hz, 1H), 2.30 (d, J=13 Hz, 1H), 2.08 (m, 1H), 1.89 (m, 2H), 1.66 (m, 1H), 1.43 (s, 9H), 1.25 (m, 1H), 1.13 (m, 1H), 1.03 (m, 1H), 0.85 (s, 9H).

Provenance & Evidence