Potassium sodium tartarate → (2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-formylpyrrolidine

HRID 439405

Reaktionsgleichung

Reaktionsgleichung von HRID 439405
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][C@H:9]1[C:24](OC)=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([NH:13][S:14]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)(=[O:15])=[O:16])[CH2:10][C@H:9]1[CH:24]=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 9855836Potassium sodium tartarateHCID 14772685(2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-methoxycarbonylpyrrolidineHCID 21225700Diisobutylaluminumhydride

Produkt 1

HCID 15670377(2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-formylpyrrolidineAusbeute 65,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of (2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-methoxycarbonylpyrrolidine (9.01 g) in toluene (70 ml) was added dropwise 1.5 molar solution of diisobutylaluminum hydride (61.2 m mol) in tetrahydrofuran (40.8 ml) at -78° C. After the mixture was stirred at -78° C. for 1.5 hours, saturated aqueous potassium sodium tartrate was added to the reaction mixture and the mixture was filtered through Celite. The solid was washed with ethyl acetate and the combined organic solution was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column with a mixture of ethyl acetate and n-hexane (1:2-2:1) as an eluent to give (2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-formylpyrrolidine (5.51 g) as pale yellow crystal.

Aufarbeitung

  1. filtrationthe mixture was filtered through Celite
  2. washThe solid was washed with ethyl acetate
  3. washthe combined organic solution was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was chromatographed on a silica gel column with a mixture of ethyl acetate and n-hexane (1:2-2:1) as an eluent

Quellen und Nachweise

ORD-Eintrag
ord-3c165684c0cd4f868b0b80497746ab99
Quelldatensatz
uspto-grants-1996_05
Patentnummer
US05514701

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