Pyridine → N-Nitroso-L-proline

HRID 262700

Reaktionsgleichung

Reaktionsgleichung von HRID 262700
[B-](F)(F)(F)F.[N:6]#[O+:7].[NH:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11].N1C=CC=CC=1>C(#N)C>[N:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 145742L-ProlineHCID 11137142Nitrilooxonium tetrafluoroborate

Produkt 1

HCID 10419304N-Nitroso-L-proline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a cooled suspension of 28.2 g. of nitrosyl tetrafluoroborate in 300 ml. of dry acetonitrile there is added, with vigorous stirring, over the course of 10 minutes, 18.4 g. of L-proline, followed by a solution of 19 g. of pyridine in 50 ml. of acetonitrile during 15 minutes. The stirring is continued for an hour and the reaction mixture is then concentrated to dryness under reduced pressure. The residue is extracted with 3×200 ml. of ethyl acetate, the ethyl acetate extracts are combined, washed twice with saturated sodium chloride solution that has been made slightly acidic with concentrated hydrochloric acid. The ethyl acetate solution is dried over anhydrous sodium sulfate, filtered and concentrated to dryness at room temperature under reduced pressure. The product, N-nitroso-L-proline metls at 108°-109° (dec.) after crystallization from a mixture of ether and petroleum ether (30°-60°).

Aufarbeitung

  1. additionTo a cooled suspension of 28.2 g
  2. waitThe stirring is continued for an hour
  3. concentrationthe reaction mixture is then concentrated to dryness under reduced pressure
  4. extractionThe residue is extracted with 3×200 ml
  5. washwashed twice with saturated sodium chloride solution that
  6. dry with materialThe ethyl acetate solution is dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness at room temperature under reduced pressure
  9. customThe product, N-nitroso-L-proline metls at 108°-109° (dec.) after crystallization
  10. additionfrom a mixture of ether and petroleum ether (30°-60°)

Quellen und Nachweise

ORD-Eintrag
ord-f743446f9c7647f482d8b7ba7cee7e0a
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04154934

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