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Formaldehyde → (Racemic)-N-[4-[3-(Acetyloxy)-1-pyrrolidinyl]-2-butynyl]-N-methyl acetamide

HRID 1534550
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1534550
[C:1]([O:4][CH:5]1[CH2:9][CH2:8][NH:7][CH2:6]1)(=[O:3])[CH3:2].[CH3:10][N:11]([CH2:15][C:16]#[CH:17])[C:12](=[O:14])[CH3:13].C=O.[C:20](=O)(O)[O-].[Na+]>ClCCl.O1CCOCC1.C(O)(=O)C>[C:1]([O:4][CH:5]1[CH2:9][CH2:8][N:7]([CH2:20][C:17]#[C:16][CH2:15][N:11]([CH3:10])[C:12](=[O:14])[CH3:13])[CH2:6]1)(=[O:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 712FormaldehydeHCID 29033Acetamide, N-methyl-N-[2-propynyl]-HCID 516892Sodium BicarbonateHCID 15046662Pyrrolidin-3-yl acetate

Produkt 1

HCID 15086787(Racemic)-N-[4-[3-(Acetyloxy)-1-pyrrolidinyl]-2-butynyl]-N-methyl acetamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176
Acetic Acid
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 1.17 g of 3-acetoxy pyrrolidine, 1.2 g of N-methyl-N-propargyl acetamide, 465 mg of paraformaldehyde, 200 mg of cuprous chloride, 1.5 ml of acetic acid and 50 ml of dioxane was stirred at reflux under argon for 75 minutes. A 100 ml portion of dichloromethane was added followed by the addition of 50 ml of 10% aqueous sodium bicarbonate. The phases were separated, sodium chloride was added to the aqueous phase and the aqueous phase was reextracted with dichloromethane. The organic solutions were combined, dried, filtered and concentrated. The residue was purified by chromatography (alumina), giving 1.43 g of the desired product as a yellow oil.

Aufarbeitung

  1. temperatureat reflux under argon for 75 minutes
  2. customThe phases were separated
  3. additionsodium chloride was added to the aqueous phase
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (alumina)

Quellen und Nachweise

ORD-Eintrag
ord-6e284beeb3c948618f09320d4fd99562
Quelldatensatz
uspto-grants-1992_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05089518

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