tert-Butanol → tert-Butyl N-[1-(4-methoxyphenyl)cyclopropyl]carbamate

Participants

Reaction Steps

A solution of 1-(4-methoxyphenyl)-1-cyclopropanecarboxylic acid (5.00 g, 26.0 mmol), diphenylphosphoryl azide (7.87 g, 28.6 mmol) and triethylamine (3.03 g, 29.9 mmol) in t-BuOH (50 ml) was heated at 100° C. for 24 h. After the solvent was evaporated in vacuo, the residue was diluted with CH2Cl2 -H2O. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined solution was washed with 10% HCl aq., sat. NaHCO3 aq. and brine, dried (MgSO4) and concentrated in vacuo to give crude product (6.86 g) as a pale yellow solid. The crude product was recrystallized from hexane-ethyl acetate to give Compound 6 (4.98 g, 73%) as a white powder solid.

Provenance & Evidence