Triethylamine → (2S,4R)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-5-methoxycarbonyl-1-pentenyl]-1-(3-pyridylmethyl)pyrrolidine

HRID 257970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 257970
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]2[CH2:16][NH:15][C@H:14](/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[N:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33]Cl)[CH:28]=1.C(N(CC)CC)C>O1CCCC1.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C@H:12]2[CH2:16][N:15]([CH2:33][C:29]3[CH:28]=[N:27][CH:32]=[CH:31][CH:30]=3)[C@H:14](/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH2:13]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 15670385(2S,4R)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-5-methoxycarbonyl-1-pentenyl]pyrrolidine

Produkt 1

HCID 15670386(2S,4R)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-5-methoxycarbonyl-1-pentenyl]-1-(3-pyridylmethyl)pyrrolidineAusbeute 56,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of (2S,4R)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-5-methoxycarbonyl-1-pentenyl]pyrrolidine (1.00 g), 3-picolylchloride hydrochloride (509 mg) and triethylamine (0.43 ml) in tetrahydrofuran (25 ml) was refluxed for 48 hours and the solution was diluted with chloroform (40 ml). The solution was washed successively with saturated aqueous sodium bicarbonate and brine, and the organic layer was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel (50 g) column with a mixture of chloroform and methanol (100:1) as an eluent to give (2S,4R)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-5-methoxycarbonyl-1-pentenyl]-1-(3-pyridylmethyl)pyrrolidine (700 mg) as a pale brown oil.

Aufarbeitung

  1. temperaturewas refluxed for 48 hours
  2. washThe solution was washed successively with saturated aqueous sodium bicarbonate and brine
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was chromatographed on a silica gel (50 g) column with a mixture of chloroform and methanol (100:1) as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-b7008c012d544367aac3f1b24e2687b5
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05264453

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