Dichloromethane → 6-chloro-4'-(3-chlorophenyl)-2'-(1-methylene-propyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

HRID 1728074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1728074
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:20]/[C:21]3[CH:26]=[C:25](F)[CH:24]=[C:23](F)[CH:22]=3)/[C:7](=[O:19])[N:8]2COCC[Si](C)(C)C)=[CH:4][CH:3]=1.[CH2:29]=[C:30]([CH:33]=[N:34][C:35]([O:37][Si](C)(C)C)=[CH2:36])[CH2:31][CH3:32].FC(F)(F)C(O)=O.C(N(C(C)C)CC)(C)C.[Cl:58]CCl>C1(C)C=CC=CC=1.CO>[Cl:1][C:2]1[CH:10]=[C:9]2[NH:8][C:7](=[O:19])[C:6]3([CH:20]([C:21]4[CH:22]=[CH:23][CH:24]=[C:25]([Cl:58])[CH:26]=4)[CH2:36][C:35](=[O:37])[NH:34][CH:33]3[C:30](=[CH2:29])[CH2:31][CH3:32])[C:5]2=[CH:4][CH:3]=1

Komponenten

8

Edukt 5

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 76567901HCID 76567901, VerbindungHCID 131727336Z-6-Chloro-3-(3,5-difluoro-benzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indol-2-one

Produkt 1

HCID 775802116-chloro-4'-(3-chlorophenyl)-2'-(1-methylene-propyl)spiro[3H-indole-3,3'-piperidine]-2,6'(1H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

In a manner similar to the method described in example 97a, 55d, E/Z-6-Chloro-3-(3,5-difluoro-benzylidene)-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-indol-2-one (0.21 g, 0.5 mmol) prepared in example 133a was reacted with 1-(1-methylene-propyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene (1 g, 5.25 mmol) prepared in example 80a in toluene, then treated with trifluoroacetic acid (5 ml) in dichloromethane, followed by treatment with diisopropylethylamine (1 mL) in methanol to give racemic (2′R,3R,4′S)-6-chloro-4′-(3-chlorophenyl)-2′-(1-methylene-propyl)spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione as a white solid (35 mg, 18% for two steps).

Quellen und Nachweise

ORD-Eintrag
ord-c08bdab7d9b4480da267ef55441abe9b
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495007B2

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