Triphenylphosphine → 4-(3-(Trifluoromethyl)-3H-diazirin-3-yl)benzenemethanamine

HRID 1425710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1425710
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2([C:33]([F:36])([F:35])[F:34])[N:32]=[N:31]2)=[CH:26][CH:25]=1)=[N+]=[N-]>C1COCC1>[F:36][C:33]([F:34])([F:35])[C:30]1([C:27]2[CH:26]=[CH:25][C:24]([CH2:23][NH2:20])=[CH:29][CH:28]=2)[N:31]=[N:32]1

Komponenten

4

Edukt 2

HCID 11776Triphenylphosphine2×HCID 858170813-[4-(Azidomethyl)phenyl]-3-(Trifluoromethyl)-3H-Diazirine

Produkt 1

HCID 109328304-(3-(Trifluoromethyl)-3H-diazirin-3-yl)benzenemethanamineAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Triphenylphosphine polymer bound (Fluka, cat #93094) (1.6 g/mol, 6.3 mmol) was added to an aqueous (378 μL, 21.0 mmol)/THF (10 mL) solution of 3-[4-(azidomethyl)phenyl]-3-(trifluoromethyl)-3H-diazirine (506 mg, 2.1 mmol). The mixture was shaken until the starting material was no longer evident by TLC analysis (18 h). The triphenylphosphine-based support was filtered, washed with CH2Cl2, and the filtrate was concentrated in vacuum to obtain 350 mg (80%) of a yellow oil corresponding to the free amine: 1H NMR (CDCl3) δ 1.35-1.50 (br s, NH2), 3.89 (s, CH2), 7.17 (d, J=8.2 Hz, 2 C6H4), 7.35 (d, J=8.2 Hz, 2 C6H4); 13C NMR (CDCl3): δ 28.4 (q, J=39.9 Hz, C diazirine), 45.9 (CH2NH2), 122.2 (q, J=273.2 Hz, CF3), 126.7 (C6H2), 127.5 (C6H2), 145.0 (C6H2) (one peak is overlapped with an other one).

Aufarbeitung

  1. customwas no longer evident by TLC analysis (18 h)
  2. filtrationwas filtered
  3. washwashed with CH2Cl2
  4. concentrationthe filtrate was concentrated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-623448c257da45cab6e813125eb7706f
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933065B2

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