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

HRID 1728074ノート

反応式

HRID 1728074 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1140Toluene溶媒

実験手順

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).

出典と根拠

ORDレコード
ord-c08bdab7d9b4480da267ef55441abe9b
出典データセット
uspto-grants-2009_02
特許番号
US07495007B2

反応ノート

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