Sodium Azide → HCID 57724945, compound

Participants

Reaction Steps

In a manner similar to the method described in example 2 (method A), rac-(1R,2S,6R)-6′-chloro-2-(3-chlorophenyl)-6-(1-methylethoxy)-spiro[cyclohexane-1,3′-[3H]indole]-2′,4(1′H)-dione (138.0 mg, 0.33 mmole) was treated with NaN3 (54.0 mg, 0.83 mmole) in the presence of TiCl4 (1.0 M in CH2Cl2, 0.33 mL) (Aldrich) in acetonitrile (10 mL) at reflux for 6 hrs, followed by chiral chromatograph to give (3S,4S,5R)-6′-chloro-5-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-3-(1-methylethoxy)-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (14.0 mg): HRMS (ES+) m/z Calcd for C22H22Cl2N2O3+H [(M+H)+]: 433.1080, Found: 433.1080; (3R,4R,5S)-6′-chloro-5-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-3-(1-methylethoxy)-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (14.0 mg): HRMS (ES+) m/z Calcd for C22H22Cl2N2O3+H [(M+H)+]: 433.1080, Found: 433.1080;

Provenance & Evidence