Water → trans-Tert-butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxypyrrolidine-1-carboxylate

HRID 1666673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1666673
C([O:4][C@H:5]1[C@H:9]([NH:10][C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:8][N:7]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+].O>CO>[CH2:14]([O:13][C:11]([NH:10][C@H:9]1[C@H:5]([OH:4])[CH2:6][N:7]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:8]1)=[O:12])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 57970174t-Butyl (3R,4R)-3-acetoxy-4-benzyloxycarbonylaminopyrrolidine-1-carboxylate

Produkt 1

HCID 57970124trans-Tert-butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxypyrrolidine-1-carboxylateAusbeute 91,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

t-Butyl (3R,4R)-3-acetoxy-4-benzyloxycarbonylaminopyrrolidine-1-carboxylate (27 g) was dissolved in methanol (350 mL), followed by addition of potassium carbonate (16 g) with ice cooling, and the mixture was stirred overnight at room temperature. Water was added, and then the mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1-2:1) to obtain t-butyl (3R,4R)-3-benzyloxycarbonylamino-4-hydroxypyrrolidine-1-carboxylate (22 g).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4:1-2:1)

Quellen und Nachweise

ORD-Eintrag
ord-5ece42eb747f405baec5313a3bff91f9
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044068B2

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