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Hydrazine hydrate (1:1) → [(S)-2-amino-2-(3-chloro-phenyl)-ethyl]-carbamic acid tert-butyl ester

HRID 595804
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 595804
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:8]([N:18]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[CH:6][CH:7]=1.O.NN>C(O)C>[NH2:18][C@@H:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 118054581(S)-tert-butyl (2-(3-chlorophenyl)-2-(1,3-dioxoisoindolin-2-yl)ethyl)carbamate

Produkt 1

HCID 69108925[(S)-2-amino-2-(3-chloro-phenyl)-ethyl]-carbamic acid tert-butyl esterAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of (S)-tert-butyl (2-(3-chlorophenyl)-2-(1,3-dioxoisoindolin-2-yl)ethyl)carbamate (5.0 g, 12.47 mmol) in ethanol (41.6 mL) was added hydrazine hydrate (6.06 mL, 125 mmol). The reaction mixture was heated at 60° C. for 2 h. The reaction mixture was filtered through Celite pad. The filtrate was concentrated and the residue was diluted with DCM and filtered off through Celite. The same process was repeated until no white precipitate was shown. To remove the white side product completely, the product was dissolved in 1N HCl (30 mL), washed with EtOAc, and the aqueous phase was neutralized to pH 7 then back-extracted by EtOAc. The organic was dried over anhydrous sodium sulfate, filtered off, and concentrated in vacuo yielding (S)-tert-butyl (2-amino-2-(3-chlorophenyl)ethyl)carbamate (89%). LCMS (m/z): 271.1 (MH+), 0.58 min.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through Celite pad
  2. concentrationThe filtrate was concentrated
  3. additionthe residue was diluted with DCM
  4. filtrationfiltered off through Celite
  5. customTo remove the white side product completely
  6. dissolutionthe product was dissolved in 1N HCl (30 mL)
  7. washwashed with EtOAc
  8. extractionthen back-extracted by EtOAc
  9. dry with materialThe organic was dried over anhydrous sodium sulfate
  10. filtrationfiltered off
  11. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-61079a0ab3704555a5a4b1a842defd8b
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09242996B2

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