Methanol → Tert-butyl 4-(2,2,2-trifluoroethyl)piperazine-1-carboxylate

HRID 1689877Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689877
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=O)[C:15]([F:18])([F:17])[F:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([F:17])([F:18])[F:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 962WaterHCID 20294522Tert-butyl 4-(2,2,2-trifluoroacetyl)piperazine-1-carboxylate

Produkt 1

HCID 16748694Tert-butyl 4-(2,2,2-trifluoroethyl)piperazine-1-carboxylateAusbeute 77,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 4-(2,2,2-trifluoro-acetyl)-piperazine-1-carboxylic acid tert-butyl ester (6.06 g) in dry THF (60 mL) was added borane dimethyl sulfide complex (4.5 ml) and the reaction mixture was heated to reflux. After 2 h the reaction mixture was cooled to 0° C. and MeOH was carefully added, followed by water. The organics were extracted into ethyl acetate, dried (MgSO4) and the solvent removed in vacuo to yield 4-(2,2,2-trifluoro-ethyl)-piperazine-1-carboxylic acid tert-butyl ester (4.46 g). Treatment with HCl in DCM/MeOH yielded the desired compound, which was isolated as the hydrochloride salt.

Aufarbeitung

  1. temperaturethe reaction mixture was heated to reflux
  2. extractionThe organics were extracted into ethyl acetate
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4026acecc52641ecbfd291eeedff8a97
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153629B2

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