Hydrazine hydrate (1:1) → Tert-butyl (2-amino-2-(3-chlorophenyl)ethyl)carbamate

HRID 1186547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1186547
[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH:9]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1)[N:10]1C(=O)C2C(=CC=CC=2)C1=O)([CH3:4])([CH3:3])[CH3:2].O.NN>C1COCC1.CO>[C:1]([O:5][C:6](=[O:28])[NH:7][CH2:8][CH:9]([NH2:10])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 68106925[2-(3-Chloro-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-carbamic acid tert-butyl ester

Produkt 1

HCID 69108731Tert-butyl (2-amino-2-(3-chlorophenyl)ethyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a stirred solution of [2-(3-chloro-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethy]-carbamic acid tert-butyl ester (2.5 g, 6.2 mmol) in THF (10 mL) and methanol (10 mL) was added hydrazine hydrate (3.1 g, 62 mmol). The mixture was heated a 55° C. for 1 hour. Then it was concentrated to dryness, dissolved in H2O (5 mL) and extracted with ethyl acetate (50 mL). The organic mixture was concentrated and purified by column chromatography (methanol:dichloromethane, 1:100) to afford [2-amino-2-(3-chloro-phenyl)-ethyl]-carbamic acid tert-butyl ester. (Yield 1.325 g, 79%). LC-MS: [M+H]+ 271.

Aufarbeitung

  1. concentrationThen it was concentrated to dryness
  2. dissolutiondissolved in H2O (5 mL)
  3. extractionextracted with ethyl acetate (50 mL)
  4. concentrationThe organic mixture was concentrated
  5. custompurified by column chromatography (methanol:dichloromethane, 1:100)

Quellen und Nachweise

ORD-Eintrag
ord-48374491a50844928927f432a8c535f4
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673905B2

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