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Formaldehyde → (R)-t-butyl 2-[3-(1-pyrrolidinyl)-1-propynyl]-1-pyrrolidinecarboxylate

HRID 359471
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 359471
[C:1]([C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])#[CH:2].O1[CH2:20][CH2:19]OCC1.[NH:21]1[CH2:25]C[CH2:23][CH2:22]1.C=O>C(O)(=O)C>[N:21]1([CH2:25][C:2]#[C:1][C@H:3]2[CH2:7][CH2:6][CH2:5][N:4]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:20][CH2:19][CH2:23][CH2:22]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 712FormaldehydeHCID 31268PyrrolidineHCID 312751,4-DioxaneHCID 10262067tert-butyl (2R)-2-ethynylpyrrolidine-1-carboxylate

Produkt 1

HCID 9860463(R)-t-butyl 2-[3-(1-pyrrolidinyl)-1-propynyl]-1-pyrrolidinecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176
Acetic Acid
Lösungsmittel

Versuchsvorschrift

A mixture of 3.5 g of (R)-2-ethynyl-1-pyrrolidinecarboxylic acid, 1,1-dimethylethyl ester, 75 ml dry dioxane, 3.0 ml pyrrolidine, 1.43 g of paraformaldehyde, 7.0 ml of glacial acetic acid and 50 mg of cuprous chloride is stirred at room temperature for 15 minutes then refluxed for 2 hours. The reaction is cooled and concentrated in vacuo. The residue is partitioned between water and methylene chloride and the pH of the mixture is adjusted to pH 11 with ammonium hydroxide. The basified reaction is extracted with methylene chloride and dried over sodium sulfate. The methylene chloride solution is passed over hydrous magnesium silicate and concentrated in vacuo to give 5.65 g of a dark yellow oil. The product is purified by chromatography using deactivated alumina as the absorbant, to give 0.55 g of the product as a pale yellow oil, [α]D26° =+100.6°±0.8 (C=1.22%, methylene chloride).

Aufarbeitung

  1. temperaturethen refluxed for 2 hours
  2. temperatureThe reaction is cooled
  3. concentrationconcentrated in vacuo
  4. customThe residue is partitioned between water and methylene chloride
  5. customThe basified reaction
  6. extractionis extracted with methylene chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e06d7eb5fe58423db558e7dc8520c73d
Quelldatensatz
uspto-grants-1991_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05001142

Notizen zur Reaktion

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