Triethylamine → 5-Bromo-1-methyl-1-indanamine

Participants

Reaction Conditions

Reaction Steps

To a solution of (rac)-5-bromo-1-methyl-indan-1-carboxylic acid (1.197 g, 4.69 mmol) in dry toluene (65 ml) was added triethylamine (570 mg, 475 μl, 5.63 mmol) and diphenylphosphoryl azide (1.33 g, 1.04 ml, 4.69 mmol) and the colorless solution was heated to reflux for 3 h. After cooling to 0° C., sodium trimethylsilanolate (9.38 ml, 9.38 mmol, 1M solution in THF) was added and the mixture was stirred for 30 minutes at room temperature. After quenching the reaction with 5% citric acid (100 ml), the pH was adjusted to 12-13 by addition of 3N NaOH and the mixture was extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried with Na2SO4 and evaporated. The remaining crude material was partitioned between 0.1N HCl and diethylether and the aqueous layer was extracted with diethylether. The pH of the aqueous layer was adjusted to 12 by addition of 0.1N NaOH and the aqueous layer was extracted three times with CH2Cl2. The combined CH2Cl2-layers were washed with brine, dried with Na2SO4 and evaporated to obtain the title compound as light yellow oil (963 mg, 91%). MS: 209.1 [M+H−NH3]+.

Provenance & Evidence