Sodium Azide → HCID 57724980, compound

HRID 1987791Notes

Reaction equation

HRID 1987791 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH:16]([C:17]([CH3:19])=[CH2:18])[CH2:15][C:14](=[O:20])[CH2:13][CH:12]3[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[N-:28]=[N+]=[N-].[Na+]>C(#N)C.Cl[Ti](Cl)(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C@:6]3([C@@H:12]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=4)[CH2:13][C:14](=[O:20])[NH:28][CH2:15][C@H:16]3[C:17]([CH3:19])=[CH2:18])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 67212933HCID 67212933, compound

Product 1

HCID 57724980HCID 57724980, compoundYield 20.8%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  1. customfollowed by chiral chromatography separation

Sources & evidence

ORD record
ord-6705caa5346b4a76930290417dd01984
Source dataset
uspto-grants-2009_06
Patent number
US07553833B2

Reaction notes

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