Methylamine → HCID 15629278, Verbindung

HRID 1614351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1614351
Cl[CH2:2][C@H:3]1[CH2:7][C@H:6](Cl)[CH2:5][N:4]1[S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[CH3:19][NH2:20]>CO>[C:15]1([CH3:18])[CH:16]=[CH:17][C:12]([S:9]([N:4]2[CH2:5][C@H:6]3[CH2:7][C@@H:3]2[CH2:2][N:20]3[CH3:19])(=[O:11])=[O:10])=[CH:13][CH:14]=1

Komponenten

4

Edukt 2

HCID 6329MethylamineHCID 14994789(2R,4S)-2-chloromethyl-4-chloro-1-(4-toluenesulfonyl)pyrrolidine

Produkt 1

HCID 15629278HCID 15629278, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A Parr bottle was charged with 0.5 g (1.29 mmol) of (2R,4S)-2-chloromethyl-4-chloro-1-(4-toluenesulfonyl)pyrrolidine and 6 ml of methanol and the bottle was tared. Methylamine gas was then bubbled through the methanol solution until 0.4 g (12.9 mol) of the gas had dissolved. The bottle was then sealed and heated to 110° C. After heating for 16 hours, the reaction was cooled and the solvent was evaporated at reduced pressure. The residual solids were partitioned between 50 ml of methylene chloride and 40 ml of 10% aqueous NaOH solution. The layers were separated and the organic layer was washed with 40 additional milliliters of 10% aqueous NaOH solution, and then dried over Na2SO4. Evaporation of the solvent under reduced pressure provided 309 mg of the desired product which represents a 90% yield. M.P.=82°-87° C. [α]D =-16.8° (c=1.038, CH3OH).

Aufarbeitung

  1. dissolutionhad dissolved
  2. customThe bottle was then sealed
  3. temperatureAfter heating for 16 hours
  4. temperaturethe reaction was cooled
  5. customthe solvent was evaporated at reduced pressure
  6. customThe residual solids were partitioned between 50 ml of methylene chloride and 40 ml of 10% aqueous NaOH solution
  7. customThe layers were separated
  8. washthe organic layer was washed with 40 additional milliliters of 10% aqueous NaOH solution
  9. dry with materialdried over Na2SO4
  10. customEvaporation of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d36aaa42fbff4cbdbdb07600c0cc02ec
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05196548

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