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Ammonium formate → Methyl 3-(methoxymethyl)pyrrolidine-3-carboxylate

HRID 1038019
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1038019
[CH3:1][O:2][C:3]([C:5]1([CH2:17][O:18][CH3:19])[CH2:9][CH2:8][N:7](CC2C=CC=CC=2)[CH2:6]1)=[O:4].C([O-])=O.[NH4+]>[Pd].CO>[CH3:1][O:2][C:3]([C:5]1([CH2:17][O:18][CH3:19])[CH2:9][CH2:8][NH:7][CH2:6]1)=[O:4]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 59511352Methyl 1-benzyl-3-(methoxymethyl)pyrrolidine-3-carboxylate

Produkt 1

HCID 59511362Methyl 3-(methoxymethyl)pyrrolidine-3-carboxylateAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 1-benzyl-3-methoxymethyl-pyrrolidine-3-carboxylic acid methyl ester (373 mg, 1.42 mmol), ammonium formate (358 mg, 5.68 mmol), 10% Pd/C (100 mg) and methanol (6 ml) was refluxed overnight. The mixture was filtered through Celite, washed with ethyl acetate. The combined filtrate was concentrated and the residue was taken into ethyl acetate, washed with small amount of water. Aqueous layer was isolated, extracted with dichloromethane three times. The dichloromethane extracts were combined with previous ethyl acetate extracts and dried over MgSO4. Evaporation of solvents provided the title compound as oil (140 mg, 57%).

Aufarbeitung

  1. temperaturewas refluxed overnight
  2. filtrationThe mixture was filtered through Celite
  3. washwashed with ethyl acetate
  4. concentrationThe combined filtrate was concentrated
  5. washwashed with small amount of water
  6. customAqueous layer was isolated
  7. extractionextracted with dichloromethane three times
  8. dry with materialdried over MgSO4
  9. customEvaporation of solvents

Quellen und Nachweise

ORD-Eintrag
ord-41c704571dfc426ba168a8f00f2e436f
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08546404B2

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