Sodium Azide → HCID 25142208, compound

HRID 1987794Notes

Reaction equation

HRID 1987794 reaction equation
ClC1C=C2C(C3(C(OC)CC(=O)CC3C3C=CC=C(Cl)C=3)C(=O)N2)=CC=1.[N-]=[N+]=[N-].[Na+].[Cl:31][C:32]1[CH:40]=[C:39]2[C:35]([C@:36]3([C@@H:47]([C:48]4[CH:53]=[CH:52][CH:51]=[C:50]([Cl:54])[CH:49]=4)[CH2:46][C:45](=[O:55])[NH:44][CH2:43][C@H:42]3[O:56][CH3:57])[C:37](=[O:41])[NH:38]2)=[CH:34][CH:33]=1>C(#N)C.Cl[Ti](Cl)(Cl)Cl>[Cl:31][C:32]1[CH:40]=[C:39]2[C:35]([C@@:36]3([C@H:47]([C:48]4[CH:53]=[CH:52][CH:51]=[C:50]([Cl:54])[CH:49]=4)[CH2:46][C:45](=[O:55])[NH:44][CH2:43][C@@H:42]3[O:56][CH3:57])[C:37](=[O:41])[NH:38]2)=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 57724941HCID 57724941, compoundHCID 67213467HCID 67213467, compound

Product 1

HCID 25142208HCID 25142208, compound

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-(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.

Sources & evidence

ORD record
ord-8fe16e2b48e346de8254d55c5379f8cf
Source dataset
uspto-grants-2009_06
Patent number
US07553833B2

Reaction notes

Loading…