Sodium Azide → HCID 25142208, compound

Participants

Reaction Steps

In a manner similar to the method described in example 2 (method A), rac-(1R,2S,6S)-6′-chloro-2-(3-chlorophenyl)-6-methoxyspiro[cyclohexane-1,3′-[3H]indole]-2′,4(1′H)-dione (156 mg, 0.4 mmol) was reacted with NaN3 (52 mg, 0.8 mmole) in the presence of TiCl4 (1.0 M in CH2Cl2, 0.8 mL) (Aldrich) in acetonitrile (10 mL) followed by chiral chromatograph to give (3R,4R,5S)-6′-chloro-5-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-3-methoxy-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (17.6 mg) and (3S,4S,5R)-6′-chloro-5-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-3-methoxy-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione.

Provenance & Evidence