Carbon Dioxide → HCID 178497106, compound

Participants

Reaction Conditions

Reaction Steps

(5-Bromo-2,3-dihydro-1H-inden-1-yl)(trans-4-tert-butylcyclohexyl)amine (1.20 g, 3.42 mmol) was dried azeotropically from dry THF in toluene (3×) and kept under high vacuum for 2 h before use. It was then dissolved in anhydrous THF (20 mL) and cooled to −78° C. n-Butyl lithium (1.6 M solution in Hexane, 8.40 mL, 13.68 mmol) was added over 15 min. After stirring at −78° C. for 30 min, excess dry ice cubes were then added. The reaction mixture was allowed to warm up slowly and then quenched at −20° C. with saturated aqueous NH4Cl (20 mL). Extractions with EtOAc (3×15 mL), drying (Na2SO4), filtration and removal of solvent gave the crude carboxylic acid. The crude carboxylic acid was dissolved in MeOH/DCM (1:2, 10 mL) and then (trimethylsilyl)diazomethane (2.0 M solution in Hexane) was added until gas bubbling ceased and the yellow color sustained. Concentration and chromatography (35% EtOAc in Hexane) afforded methyl 1-[(trans-4-tert-butylcyclohexyl)amino]indane-5-carboxylate. HPLC/MS: m/z=330.3 (M+1), Rt=2.85 min.

Provenance & Evidence