Dimethyl Sulfoxide → (3R,4S)-1-benzyl-4-phenylpyrrolidine-3-carbaldehyde

HRID 732713

Reaktionsgleichung

Reaktionsgleichung von HRID 732713
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([N:18]1[CH2:22][C@H:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@@H:20]([CH2:29][OH:30])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl.O>[CH2:11]([N:18]1[CH2:22][C@H:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C@@H:20]([CH:29]=[O:30])[CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 21341047((3R,4S)-1-Benzyl-4-phenylpyrrolidin-3-YL)methanol

Produkt 1

HCID 54388031(3R,4S)-1-benzyl-4-phenylpyrrolidine-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A 0.43 ml portion of DMSO was dissolved in 6 ml of dichloromethane, and a 3 ml dichloromethane solution of 0.26 ml of oxalyl chloride was added thereto while keeping the internal temperature at −60° C. or less. After 30 minutes of stirring, a 10 ml dichloromethane solution of 270 mg of [(3R,4S)-1-benzyl-4-phenylpyrrolidin-3-yl]methanol which had been synthesized in accordance with the technique of Ling et al. (“Tetrahedron”, 2001, vol. 57, p. 6579-6588) and the method of International Patent Publication WO 2000/59502 was added thereto while keeping the internal temperature at −60° C. or less and stirred for 30 minutes. A 1.27 ml portion of triethylamine was added to the reaction solution while keeping the internal temperature at −50° C. or less, and then the internal temperature was allowed to warm to 0° C. over 30 minutes or more, and this was stirred at 0° C. for 30 minutes. The reaction solution was mixed with water to quench the reaction and extracted with chloroform. The organic layer was washed with saturated brine and dried with anhydrous sodium sulfate. This was concentrated under a reduced pressure to obtain (3R,4S)-1-benzyl-4-phenylpyrrolidine-3-carboaldehyde as a crude product.

Aufarbeitung

  1. customat −60° C. or less
  2. additionthe method of International Patent Publication WO 2000/59502 was added
  3. customat −60° C. or less
  4. stirringstirred for 30 minutes
  5. customat −50° C. or less
  6. stirringthis was stirred at 0° C. for 30 minutes
  7. customto quench
  8. customthe reaction
  9. extractionextracted with chloroform
  10. washThe organic layer was washed with saturated brine
  11. dry with materialdried with anhydrous sodium sulfate
  12. concentrationThis was concentrated under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-18fcf17e0d874df9b8416e6147be10d0
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07585886B2

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