Trifluoroacetic acid → Ethyl 4-benzylpiperidine-4-carboxylate

HRID 2179809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2179809
[CH2:1]([C:8]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([C:8]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 162182711-tert-Butyl 4-ethyl 4-benzylpiperidine-1,4-dicarboxylate

Produkt 1

HCID 53297794Ethyl 4-benzylpiperidine-4-carboxylateAusbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 1-tert-butyl 4-ethyl 4-benzylpiperidine-1,4-dicarboxylate (step 2, 4.5 g, 12.96 mmol) in DCM (50 ml) was cooled to 0° C. After ten minutes, trifluoroacetic acid (6.0 g) was added and stirred the reaction at room temperature for about 6 hours. After completion of the reaction (monitored by TLC), the reaction mixture was neutralized with sat. NaHCO3, extracted with DCM, dried over Na2SO4 and concentrated under reduced pressure to furnish the title compound (2.3 g) as a light yellow liquid. 1H NMR (300 MHz, CDCl3): 1.19-1.24 (t, 3H); 1.48-1.58 (m, 2H); 2.14-2.18 (m, 2H); 2.64-2.73 (m, 2H); 2.86 (s, 2H); 3.01-3.07 (m, 4H); 4.10-4.17 (m, 2H); 7.07-7.10 (m, 2H); 7.24-7.30 (m, 3H); ES Mass: 248 (100%) [M+1].

Aufarbeitung

  1. waitAfter ten minutes
  2. customthe reaction at room temperature for about 6 hours
  3. customAfter completion of the reaction (monitored by TLC)
  4. extractionextracted with DCM
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-19f9bd00084448f5b52e1726b514501b
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067966B2

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