Sodium Azide → HCID 86624804, compound

HRID 1987792Notes

Reaction equation

HRID 1987792 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([CH:16]([C:17]([CH3:20])=[CH:18][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([CH:16](/[C:17](/[CH3:20])=[CH:18]/[CH3:19])[CH2:15][C:14](=[O:21])[NH:29][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

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 67212875HCID 67212875, compound

Product 1

HCID 86624804HCID 86624804, compoundYield 10.8%

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-methyl-propenyl)spiro[cyclohexane-1,3′-[3H]indole]-2′,4(1′H)-dione (120 mg, 0.29 mmol) was reacted with NaN3 (47.1 mg, 0.72 mmole) in the presence of TiCl4 (1.0 M in CH2Cl2, 0.29 mL) (Aldrich) in acetonitrile (10 mL) followed by chiral chromatography separation to give 3R,4S,5S)-6′-chloro-3-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-5(E)-(1-methyl-1-propenyl)-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (13.5 mg): HRMS (ES+) m/z Calcd for C23H22Cl2N2O2+H [(M+H)+]: 429.1131. Found: 429.1131; (3R,4S,5S)-6′-chloro-5-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-3(E)-(1-methyl-1-propenyl)-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (15.8 mg): HRMS (ES+) m/z Calcd for C23H22Cl2N2O2+H [(M+H)+]: 429.1131. Found: 429.1131; (3S,4R,5R)-6′-chloro-3-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-5(E)-(1-methyl-1-propenyl)-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (13.7 mg): HRMS (ES+) m/z Calcd for C23H22Cl2N2O2+H [(M+H)+]: 429.1131. Found: 429.1131; and (3S,4R,5R)-6′-chloro-5-(3-chlorophenyl)-1,1′,2,2′,3,5,6,7-octahydro-3(E)-(1-methyl-1-propenyl)-spiro[4H-azepine-4,3′-[3H]-indole]-2′,7-dione (14.5 mg): HRMS (ES+) m/z Calcd for C23H22Cl2N2O2+H [(M+H)+]: 429.1131. Found: 429.1131.

Workup

  1. customfollowed by chiral chromatography separation

Sources & evidence

ORD record
ord-8b9459f3368e42639d6873ed95edafa1
Source dataset
uspto-grants-2009_06
Patent number
US07553833B2

Reaction notes

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