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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
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 602761
[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
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 125044-Methylphenylhydrazine monohydrochlorideHCID 516892Sodium BicarbonateHCID 13075147HCID 13075147, Verbindung

Produkt 1

HCID 11291893(RS,SR)-2-benzenesulfonyl-2-(6-methyl-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propionitrileAusbeute 29,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic Acid
Lösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3991456d9cac4c23a52850e8bde57ca7
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07906546B2

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