Sodium Azide → HCID 25142484, 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-(3-methylphenyl)spiro[cyclohexane-1,3′-[3H]indole]-2′,4(1′H)-dione (140 mg, 0.31 mmol) was reacted with NaN3 (50.1 mg, 0.78 mmole) in the presence of TiCl4 (1.0 M in CH2Cl2, 0.31 mL) (Aldrich) in acetonitrile (10 mL) followed by chiral chromatograph to give (3S,4R,5R)-6′-chloro-3-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-5-(3-methylphenyl)-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (11.2 mg): HRMS (ES+) m/z Calcd for C26H22Cl2N2O2+H [(M+H)+]: 465.1131. Found: 465.1132; (3S,4R,5R)-6′-chloro-5-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-3-(3-methylphenyl)-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (10.7 mg): HRMS (ES+) m/z Calcd for C26H22Cl2N2O2+H [(M+H)+]: 465.1131. Found: 465.1131; (3R,4S,5S)-6′-chloro-3-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-5-(3-methylphenyl)-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (10.3 mg): HRMS (ES+) m/z Calcd for C26H22Cl2N2O2+H [(M+H)+]: 465.1131. Found: 465.1131; and (3R,4S,5S)-6′-chloro-5-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-3-(3-methylphenyl)-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (10.1 mg): HRMS (ES+) m/z Calcd for C26H22Cl2N2O2+H [(M+H)+]: 465.1131. Found: 465.1131.

Provenance & Evidence