Trifluoroacetic acid → HCID 71279749, Verbindung

HRID 246162Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 246162
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]#[N:15])[CH2:9]1)(C)(C)C.[F:17][C:18]([F:23])([F:22])[C:19]([OH:21])=[O:20]>ClCCl>[F:17][C:18]([F:23])([F:22])[C:19]([OH:21])=[O:20].[NH2:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]#[N:15])[CH2:9]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 71279909HCID 71279909, Verbindung

Produkt 1

HCID 71279749HCID 71279749, VerbindungAusbeute 142,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a 25 mL round-bottomed flask, cis-(3-cyano-cyclohexyl)-carbamic acid tert-butyl ester (212 mg, 0.945 mmol) was combined with dichloromethane (3 ml) to give a colorless solution. Trifluoroacetic acid (0.9 mL, 11.7 mmol) was added to give a yellow solution which was stirred at room temperature for 1.5 h. The reaction mixture was then concentrated under reduced pressure. The residue was azeotroped with toluene to afford 321 mg of cis-3-aminocyclohexanecarbonitrile trifluoroacetate as a crude solid that was taken to the next step without purification. 1H NMR (300 MHz, DMSO-d6) δ: 7.96 (br. s., 3H), 2.93-3.14 (m, 1H), 2.87 (tt, J=12.2, 3.5 Hz, 1H), 2.22 (d, J=12.1 Hz, 1H), 1.96 (d, J=10.2 Hz, 1H), 1.87 (d, J=11.3 Hz, 1H), 1.68-1.81 (m, 1H), 1.49 (q, J=12.1 Hz, 1H), 1.18-1.41 (m, 3H).

Aufarbeitung

  1. customto give a colorless solution
  2. customto give a yellow solution which
  3. concentrationThe reaction mixture was then concentrated under reduced pressure
  4. customThe residue was azeotroped with toluene

Quellen und Nachweise

ORD-Eintrag
ord-82586e0cc5994bbdad5c4661f240ac64
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658646B2

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