8-Chloro-1-(4-oxo-cyclohexyl)-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester → 8-Chloro-1-(4-hydroxy-4-o-tolyl-cyclohexyl)-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester

HRID 1255455ノート

反応式

HRID 1255455 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:17][C:16]2[N:12]([C:13]([CH:18]3[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]3)=[N:14][N:15]=2)[C:11]2[CH:25]=[CH:26][C:27]([Cl:29])=[CH:28][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:30]1([CH3:38])[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[Mg]Cl>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:17][C:16]2[N:12]([C:13]([CH:18]3[CH2:19][CH2:20][C:21]([OH:24])([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[CH3:38])[CH2:22][CH2:23]3)=[N:14][N:15]=2)[C:11]2[CH:25]=[CH:26][C:27]([Cl:29])=[CH:28][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 584587428-Chloro-1-(4-oxo-cyclohexyl)-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl esterHCID 178424304HCID 178424304、化合物

生成物 1

HCID 584587368-Chloro-1-(4-hydroxy-4-o-tolyl-cyclohexyl)-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester収率 70%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 8-chloro-1-(4-oxo-cyclohexyl)-4H,6H-2,3,5,10b-tetraaza-benzo[e]azulene-5-carboxylic acid tert-butyl ester (0.2 g, 0.5 mmol) in dry tetrahydrofuran (5 ml) was added a 1M o-tolylmagnesium chloride solution in tetrahydrofuran (0.5 ml, 0.5 mmol) at room temperature. After stirring for 2 h the reaction mixture was quenched with aqueous saturated ammonium chloride solution and extracted with two portions of ethyl acetate. The combined organic layers were washed with one portion of brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Flash-chromatography with n-heptane/ethyl acetate as eluent gave the title compound (0.17 g, 70%) as white solid. MS m/e: 509 ([[M+H]]+)

後処理

  1. customwas quenched with aqueous saturated ammonium chloride solution
  2. extractionextracted with two portions of ethyl acetate
  3. washThe combined organic layers were washed with one portion of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-84406677a40b4b55a69c8a103b306231
出典データセット
uspto-grants-2013_06
特許番号
US08461151B2

反応ノート

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