Sodium Azide → HCID 68907246, compound

HRID 1987793Notes

Reaction equation

HRID 1987793 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH:16]([O:17][CH3:18])[CH2:15][C:14](=[O:19])[CH2:13][CH:12]3[C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[N-:27]=[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([CH:16]([O:17][CH3:18])[CH2:15][C:14](=[O:19])[NH:27][CH2:13][CH:12]3[C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 67212910HCID 67212910, compound

Product 1

HCID 68907246HCID 68907246, compoundYield 5.7%

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,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.

Sources & evidence

ORD record
ord-733407adef20491aa8c468bbc33b251d
Source dataset
uspto-grants-2009_06
Patent number
US07553833B2

Reaction notes

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