Trifluoroacetic acid → Ethyl 2-((cyclopentylamino)methyl)-2-fluorobutanoate

HRID 1880935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1880935
C([N:8]([CH2:14][C:15]([F:23])([CH2:21][CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1)C1C=CC=CC=1.C(O)(C(F)(F)F)=O>C(O)C.[OH-].[OH-].[Pd+2]>[CH:9]1([NH:8][CH2:14][C:15]([F:23])([CH2:21][CH3:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:10][CH2:11][CH2:12][CH2:13]1

Komponenten

5

Edukt 2

HCID 6422Trifluoroacetic acidHCID 57955532Ethyl 2-((benzyl(cyclopentyl)amino)methyl)-2-fluorobutanoate

Produkt 1

HCID 57955590Ethyl 2-((cyclopentylamino)methyl)-2-fluorobutanoateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9942167Palladium hydroxideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of ethyl 2-((benzyl(cyclopentyl)amino)methyl)-2-fluorobutanoate (2.2 g, 6.8 mmol) in ethanol (20 mL) was hydrogenated with Pd(OH)2 (20%, 240 mg, 0.34 mmol) in presence of TFA (6.8 mmol) at atmospheric pressure for 20 h. The reaction mixture was filtered through celite. The filtrate was concentrated and diluted to EtOAc/H2O, aqueous layer was basified to pH=11-12 by 1N NaOH. The organic layer was then dried and concentrated to give the product (1.38 g, 88%) as light yellow liquid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.95 (t, J=7.6 Hz, 3 H) 1.31 (t, J=7.1 Hz, 4 H) 1.41-1.94 (m, 9 H) 2.88-3.08 (m, 3 H) 4.26 (qd, J=7.12, 2.40 Hz, 2 H). [M+H] calc'd for C12H22FNO2, 232; found 232.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationThe filtrate was concentrated
  3. additiondiluted to EtOAc/H2O, aqueous layer
  4. customThe organic layer was then dried
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e4f6e835d6b2431a8253c7b65b283e45
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318727B2

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