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Cerium(III) chloride → Racemic (10,11-Dihydro-5H-pyrrolo[2,1-c](1,4]benzodiazepin-10-yl)-[4-(3-hydroxy-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-methanone

HRID 1793973
ノート
印刷プレビュー

反応式

HRID 1793973 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH2:14][N:13]3[CH:21]=[CH:22][CH:23]=[C:12]3[CH2:11]2)=[O:9])[CH:5]=[CH:4][C:3]=1[C:24]1[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[C:25]=1[CH3:31].[Cl-].[Ce+3].[Cl-].[Cl-].[BH4-].[Na+]>CO>[CH:23]1[CH:22]=[CH:21][N:13]2[CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:10]([C:8]([C:6]3[CH:5]=[CH:4][C:3]([C:24]4[CH2:29][CH2:28][CH2:27][CH:26]([OH:30])[C:25]=4[CH3:31])=[C:2]([CH3:1])[CH:7]=3)=[O:9])[CH2:11][C:12]=12
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 102950443-[4-(5H,11H-Benzo[e]pyrrolo[1,2-a][1,4]diazepine-10-carbonyl)-2-methyl-phenyl]-2-methyl-cyclohex-2-enone

生成物 1

HCID 10273123Racemic (10,11-Dihydro-5H-pyrrolo[2,1-c](1,4]benzodiazepin-10-yl)-[4-(3-hydroxy-2-methyl-cyclohex-1-en-1-yl)-3-methyl-phenyl]-methanone収率 88.1%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

実験手順

3-[2-Methyl-4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-yl-carbonyl)phenyl]-2-methyl-cyclohex-2-en-1-one of Example 4 (0.350 g, 0.853 mmol), and cerium (III) chloride (0.210 g, 0.853 mmol) were combined in methanol (4.3 mL) followed by addition of sodium borohydride (0.032 g, 0.853 mmol). The reaction was stirred at room temperature until gas evolution ceased (approximately 2 minutes), then quenched with 0.1 N hydrochloric acid (100 mL), causing a white precipitate to form. The precipitate was filtered and purified by flash column chromatography on silica gel eluting with 50% ethyl acetate in hexane to afford 0.310 g of the title alcohol as a white solid.

後処理

  1. custom(approximately 2 minutes)
  2. customquenched with 0.1 N hydrochloric acid (100 mL)
  3. customto form
  4. filtrationThe precipitate was filtered
  5. custompurified by flash column chromatography on silica gel eluting with 50% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-d972ce00f79b4617aa34722373f67965
出典データセット
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07022699B2

反応ノート

読み込み中…

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