Sodium Azide → HCID 68907246, compound

Participants

Reaction Steps

In a manner similar to the method described in example 2 (method A), rac-(1R,2S,6S)-6′-chloro-2-(4-chlorophenyl)-6-methoxyspiro[cyclohexane-1,3′-[3H]indole]-2′,4(1′H)-dione (312 mg, 0.8 mmol) was reacted with NaN3 (104 mg, 1.6 mmole) in the presence of TiCl4 (1.0 M in CH2Cl2, 0.8 mL) (Aldrich) in acetonitrile (20 mL) to give rac-(3S,4R,5S)-6′-chloro-3-(4-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-5-methoxy-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (18.6 mg): HRMS (ES+) m/z Calcd for C20H18Cl2N2O3+H [(M+H)+]: 405.0767. Found: 405.0768; and rac-(3R,4R,5S)-6′-chloro-5-(4-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-3-methoxy-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (19.7 mg): HRMS (ES+) m/z Calcd for C20H18Cl2N2O3+H [(M+H)+]: 405.0767. Found: 405.0768.

Provenance & Evidence