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4-Methylphenylhydrazine monohydrochloride → (RS,SR)-2-benzenesulfonyl-2-(6-methyl-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propionitrile

HRID 602761
ノート
印刷プレビュー

反応式

HRID 602761 の反応式
[C:1]1([S:7]([C:10]([CH:14]2[CH2:19][CH2:18][CH2:17][C:16](=O)[CH2:15]2)([CH3:13])[C:11]#[N:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29]N)=[CH:25][CH:24]=1.C([O-])(O)=O.[Na+]>C(O)(=O)C>[C:1]1([S:7]([C:10]([CH:14]2[CH2:19][CH2:18][C:17]3[C:27]4[C:26](=[CH:25][CH:24]=[C:23]([CH3:22])[CH:28]=4)[NH:29][C:16]=3[CH2:15]2)([CH3:13])[C:11]#[N:12])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
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 125044-Methylphenylhydrazine monohydrochlorideHCID 516892Sodium BicarbonateHCID 13075147HCID 13075147、化合物

生成物 1

HCID 11291893(RS,SR)-2-benzenesulfonyl-2-(6-methyl-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propionitrile収率 29.5%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

To 322 mg (1.10 mmol) of 2-benzenesulfonyl-2-(3-oxo-cyclohexyl)-propionitrile in 10 mL of glacial acetic acid, 193 mg (1.21 mmol, 1.1 eq) of (4-methyl-phenyl)-hydrazine hydrochloride were added and stirring was continued at RT over night. An aqueous solution of NaHCO3 was added until pH=7, and the product was extracted with EtOAc, the organic phase was dried over Na2SO4, filtered and evaporated. The resulting two diastereomers were separated by column chromatography on silica gel with AcOEt/heptane 1:4, and triturated with Et2O. 158 mg (38%) of (RR,SS)-2-benzenesulfonyl-2-(6-methyl-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propionitrile and 123 mg (29%) of (RS,SR)-2-benzenesulfonyl-2-(6-methyl-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propionitrile were isolated as light yellow solids, MS: 379 (MH+).

後処理

  1. waitwas continued at RT over night
  2. extractionthe product was extracted with EtOAc
  3. dry with materialthe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting two diastereomers were separated by column chromatography on silica gel with AcOEt/heptane 1:4
  7. customtriturated with Et2O

出典と根拠

ORDレコード
ord-3991456d9cac4c23a52850e8bde57ca7
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07906546B2

反応ノート

読み込み中…

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