Sodium Azide → HCID 57724945, compound

HRID 1987809Notes

Reaction equation

HRID 1987809 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH:16]([O:17][CH:18]([CH3:20])[CH3:19])[CH2:15][C:14](=[O:21])[CH2:13][CH:12]3[C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[N-:29]=[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:22]4[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=4)[CH2:13][C:14](=[O:21])[NH:29][CH2:15][C@H:16]3[O:17][CH:18]([CH3:20])[CH3:19])[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 68903252HCID 68903252, compound

Product 1

HCID 57724945HCID 57724945, compoundYield 9.8%

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-(1-methylethoxy)-spiro[cyclohexane-1,3′-[3H]indole]-2′,4(1′H)-dione (138.0 mg, 0.33 mmole) was treated with NaN3 (54.0 mg, 0.83 mmole) in the presence of TiCl4 (1.0 M in CH2Cl2, 0.33 mL) (Aldrich) in acetonitrile (10 mL) at reflux for 6 hrs, followed by chiral chromatograph to give (3S,4S,5R)-6′-chloro-5-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-3-(1-methylethoxy)-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (14.0 mg): HRMS (ES+) m/z Calcd for C22H22Cl2N2O3+H [(M+H)+]: 433.1080, Found: 433.1080; (3R,4R,5S)-6′-chloro-5-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-3-(1-methylethoxy)-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (14.0 mg): HRMS (ES+) m/z Calcd for C22H22Cl2N2O3+H [(M+H)+]: 433.1080, Found: 433.1080;

Workup

  1. temperatureat reflux for 6 hrs

Sources & evidence

ORD record
ord-a9236c85769749ed9b6f3bd137892c36
Source dataset
uspto-grants-2009_06
Patent number
US07553833B2

Reaction notes

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