1,4-Dioxane → (1S)-2-azido-1-phenylethanamine

HRID 2369818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2369818
[N:1]([CH2:4][C@@H:5]([NH:12]C(=O)OC(C)(C)C)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[N+:2]=[N-:3].O1CCOCC1>C1COCC1.Cl.CCOCC>[N:1]([CH2:4][C@@H:5]([NH2:12])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[N+:2]=[N-:3]

Komponenten

6

Edukt 2

HCID 312751,4-DioxaneHCID 86762376HCID 86762376, Verbindung

Produkt 1

HCID 10953837(1S)-2-azido-1-phenylethanamineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl [(1S)-2-azido-1-phenylethyl]carbamate (210 mg, 0.8 mmol, 1.0 eq.) in THF (2 ml), 4.0M hydrogen chloride in dioxane (2.0 ml, 8.0 mmol, 10.0 eq.) was added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ether. The precipitate was filtered and washed with ether to yield (S)-2-Azido-1-phenyl-ethylamine 40 as a white solid in 85% yield. LC-MS [163 (M+1)]

Aufarbeitung

  1. filtrationThe precipitate was filtered
  2. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-6028b2eaf91d40dd93fb9a8472577295
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710044B2

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