Dimethyl Sulfoxide → 1-Benzyl-3-(SR)-formyl-4-(RS)-(3-thienyl)pyrrolidine

HRID 380462Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 380462
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]1[CH2:22][CH:21]([C:23]2[CH:27]=[CH:26][S:25][CH:24]=2)[CH:20]([CH2:28][OH:29])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCOCC>C(Cl)Cl>[CH2:11]([N:18]1[CH2:22][CH:21]([C:23]2[CH:27]=[CH:26][S:25][CH:24]=2)[CH:20]([CH:28]=[O:29])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 3283Diethyl EtherHCID 65578Oxalyl chlorideHCID 183647731-Benzyl-3-(SR)-hydroxymethyl-4-(RS)-(3-thienyl)pyrrolidine

Produkt 1

HCID 183647191-Benzyl-3-(SR)-formyl-4-(RS)-(3-thienyl)pyrrolidineAusbeute 100,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 0.31 mL (3.6 mmol) of oxalyl chloride in 20 mL of CH2Cl2 at −78° C. was added 0.51 mL (7.2 mmol) of DMSO and the reaction mixture was stirred. After 10 min., a solution of 0.49 g (1.8 mmol) of 1-benzyl-3-(RS)-hydroxymethyl-4-(SR)-(3-thienyl)pyrrolidine in 20 mL of CH2Cl2 was then added. After stirring for 10 min. at −78° C., the reaction was allowed to warm to rt. The reaction mixture was poured into ether and extracted twice with sat'd NaHCO3 solution and once with sat'd NaCl solution. The organic fraction was dried over Na2SO4, filtered and the filtrate was concentrated to give 0.49 g of the title compound. 1H NMR (CDCl3) δ9.75 (d, 1H, J=2.1 Hz), 7.27-7.36 (m, 6H), 7.03-7.07 (m, 2H), 3.78 (q, 1H, J=6.8 Hz), 3.72 (d, 1H, J=13.1 Hz), 3.68 (d, 1H, J=12.8 Hz).

Aufarbeitung

  1. stirringAfter stirring for 10 min. at −78° C.
  2. extractionextracted twice with sat'd NaHCO3 solution and once with sat'd NaCl solution
  3. dry with materialThe organic fraction was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-0d4329a82af54145996d2ce0b9ec94f5
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303593B1

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