Trifluoroacetic acid → HCID 19925593, Verbindung

HRID 1647507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1647507
C(OC([NH:8][C:9]1[CH:10]=[C:11]([C:15]2([OH:21])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:12]=[CH:13][CH:14]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][C:9]1[CH:10]=[C:11]([C:15]2([OH:21])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:12]=[CH:13][CH:14]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 19925596HCID 19925596, Verbindung

Produkt 1

HCID 19925593HCID 19925593, VerbindungAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To an ice-cooled solution of 4-(3-t-butyloxycarbonylaminophenyl)-4-hydroxytetrahydropyran (2.0 g, 6.8 mmol), prepared as in step 2, in dichloromethane (14 mL) was added trifluoroacetic acid (14, mL). The resulting solution was stirred for 0.25 hours at 0° C. and 1 hour at ambient temperature. The volatiles were removed in vacuo and the resulting solution was basified with saturated aqueous potassium carbonate. The resulting mixture was diluted with dichloromethane and the layers separated. The aqueous layer was extracted (4×, dichloromethane). The combined organic layers were dried (MgSO4), and concentrated in vacuo to provide a solid. Trituration with hexanes provided 4-(3-aminophenyl)-4-hydroxytetrahydropyran as a colorless solid (1.01 g, 77%). mp 154°-155° C. 1H NMR (300 MHz, CDCl3) δ7.17 (1H, dt, J=7.5, 1 Hz), 6.84-6.88 (2H, m), 6.62 (1H, br d, J=7.5 Hz), 3.93 (2H, td, J=12, 12, 2.5 Hz), 3.84 (2H, ddd, J=12, 5, 1.5 Hz), 2.05-32 (4H, m). MS m/e 193 (M+NH4 --H2O)+, 211 (M+NH4)+.

Aufarbeitung

  1. customThe volatiles were removed in vacuo
  2. additionThe resulting mixture was diluted with dichloromethane
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted (4×, dichloromethane)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto provide a solid

Quellen und Nachweise

ORD-Eintrag
ord-aca13c46b86c4fa0ab69e3d54f7ff314
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05432194

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