Trifluoroacetic acid → 2-(Pyrrolidin-1-yl)carbonyl-3-hydroxy piperidine

HRID 1534439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1534439
[N:1]1([C:6]([C:8]2[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][N:9]=2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[H][H]>C(O)(=O)C.O=[Pt]=O>[N:1]1([C:6]([CH:8]2[CH:13]([OH:14])[CH2:12][CH2:11][CH2:10][NH:9]2)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 3

HCID 6422Trifluoroacetic acidHCID 19909697(3-Hydroxypyridin-2-yl)(pyrrolidin-1-yl)methanoneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 151657872-(Pyrrolidin-1-yl)carbonyl-3-hydroxy piperidineAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

10 g (0.052 moles) of 2-(pyrrolidin-1-yl)carbonyl-3-hydroxy pyridine, dissolved in 100 ml of acetic acid and 8 mml of trifluoroacetic acid, were hydrogenated at 40 psi over 1 g of PtO2 at room temperature, until the theoretical amount of hydrogen was consumed. The catalyst was filtered off and the filtrate evaporated in vacuo. The residue was taken up in 20% NaOH and extracted with CH2Cl2, which was dried and evaporated in vacuo to dryness. 8.5 g of the title compound were obtained as a 80/20 diastereoisomeric mixture, which was used for the subsequent step without further purification.

Aufarbeitung

  1. customwas consumed
  2. filtrationThe catalyst was filtered off
  3. customthe filtrate evaporated in vacuo
  4. extractionextracted with CH2Cl2, which
  5. customwas dried
  6. customevaporated in vacuo to dryness

Quellen und Nachweise

ORD-Eintrag
ord-bab05b11d7ce425b88aaacceb137d02d
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05089507

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