Trifluoroacetic acid → 1-(4-(Azetidin-3-yloxy)benzyl)pyrrolidine

HRID 1035165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1035165
[N:1]1([CH2:6][C:7]2[CH:24]=[CH:23][C:10]([O:11][CH:12]3[CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]3)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:14]1[CH2:13][CH:12]([O:11][C:10]2[CH:23]=[CH:24][C:7]([CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:8][CH:9]=2)[CH2:15]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 58043117Tert-butyl 3-(4-(pyrrolidin-1-ylmethyl)phenoxy)azetidine-1-carboxylate

Produkt 1

HCID 670165201-(4-(Azetidin-3-yloxy)benzyl)pyrrolidineAusbeute 86,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1A (5.2 g, 15.5 mmol) in DCM (50 mL) was treated with TFA (10 g, 88 mmol) and stirred at RT for 17 h. The reaction mixture was concentrated and then co-evaporated using DCM. The residue was dissolved in water and the pH adjusted to pH 10 by adding NaOH. The solution was extracted several times with DCM and the organic solutions were filtered through a phase separator. The solvent was removed by evaporation. There was obtained 3.1 g (85%) of 1B as an oil. 1H NMR (500 MHz, CDCl3): δ 1.69-1.83 (m, 4H), 2.43-2.57 (m, 4H), 3.53 (s, 2H), 3.73-3.81 (m, 2H), 3.87-3.92 (m, 2H), 4.93-5.01 (m, 1H), 6.68 (d, 2H), 7.20 (d, 2H).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in water
  3. additionby adding NaOH
  4. extractionThe solution was extracted several times with DCM
  5. filtrationthe organic solutions were filtered through a phase separator
  6. customThe solvent was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-4420dbdacbd1460d837bd5aa37816600
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546375B2

Notizen zur Reaktion

Wird geladen…