1,2-Dichloroethane → HCID 178450646, compound

Participants

Reaction Steps

To a solution of butyl 1-[(trans-4-tert-butylcyclohexyl)amino]indane-5-carboxylate (0.30 g, 0.81 mmol) in DMF/CH2CL2 (1:1, 10 mL) was added [4-(trifluoromethoxy)phenyl]acetic acid (0.21 g, 0.97 mmol), EDC (0.20 g, 1.05 mmol), HOBt (0.11 g, 0.81 mmol) and DIEA (0.45 mL, 2.43 mmol). After stirring at room temperature for 18 h, the reaction mixture was poured into saturated aqueous NaHCO3 (20 mL) and extracted with EtOAc (30 mL). The organic layer was washed with brine (2×10 mL), dried over Na2SO4, filtered and concentrated. Chromatography (10% to 20% EtOAc in Hexane) gave 0.39 g (84% yield) of butyl 1-((trans-4-tert-butylcyclohexyl){[4-(trifluoromethoxy)phenyl]acetyl}amino)indane-5-carboxylate. HPLC/MS: m/z=574.2 (M+1), Rt=3.19 min. The racemic compound was then resolved on chiral HPLC (ChiralPak AD column, 5% EtOH in n-Heptane) to give enantiomer A (+) (Rt=8.65 min) and B (−) (Rt=12.0 min).

Provenance & Evidence