Sodium Azide → HCID 57724980, 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-iso-propenylspiro[cyclohexane-1,3′-[3H]indole]-2′,4(1′H)-dione (120 mg, 0.3 mmol) was reacted with NaN3 (39 mg, 0.6 mmole) in the presence of TiCl4 (1.0 M in CH2Cl2, 0.3 mL) (Aldrich) in acetonitrile (10 mL) followed by chiral chromatography separation to give (3S,4R,5R)-6′-chloro-5-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-3-(1-methylethenyl)-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (25.9 mg): HRMS (ES+) m/z Calcd for C22H20Cl2N2O2+H [(M+H)+]: 415.0975, Found: 415.0974; (3R,4S,5S)-6′-chloro-5-(3-chlorophenyl))-1,1′,2,2′,3,5,6,7-octahydro-3-(1-methylethenylspiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (28.8 mg): HRMS (ES+) m/z Calcd for C22H20Cl2N2O2+H [(M+H)+]: 415.0975, found: 415.0975; (3S,4R,5R)-4′-chloro-3-(3-chlorophenyl))-1,1′,2,2′,3,5,6,7-octahydro-5-(1-methylethenylspiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (20.7 mg): HRMS (ES+) m/z Calcd for C22H20Cl2N2O2+H [(M+H)+]: 415.0975, found: 415.0974; and (3R,4S,5S)-6′-chloro-3-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-5-(1-methylethenyl)-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (21.6 mg): HRMS (ES+) m/z Calcd for C22H20Cl2N2O2+H [(M+H)+]: 415.0975, found: 415.0974.

Provenance & Evidence