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

HRID 338960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338960
[NH2:1][C@H:2]1[C@H:6]([OH:7])[CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.C([O-])([O-])=O.[Na+].[Na+].[CH:21]1[CH:26]=[CH:25][C:24]([CH2:27][O:28][C:29](Cl)=[O:30])=[CH:23][CH:22]=1.C(OCC)(=O)C>O1CCOCC1.O>[CH2:27]([O:28][C:29]([NH:1][C@H:2]1[C@H:6]([OH:7])[CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1)=[O:30])[C:24]1[CH:25]=[CH:26][CH:21]=[CH:22][CH:23]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 11275699(3R,4R)-3-Amino-1-Boc-4-hydroxypyrrolidine

Produkt 1

HCID 57970124trans-Tert-butyl 3-(((benzyloxy)carbonyl)amino)-4-hydroxypyrrolidine-1-carboxylateAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of (3R,4R)-tert-butyl 3-amino-4-hydroxypyrrolidine-1-carboxylate (4.40 g, 21.76 mmol) and Na2CO3 (2.77 g, 26.11 mmol) in dioxane (50 mL) and water (50 mL) was added Cbz-Cl (3.87 mL, 26.11 mmol) at 0° C. The reaction mixture was warmed to ambient temperature and stirred at ambient temperature for 3 hours. Ethyl acetate (50 mL) was added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate) to give (3R,4R)-tert-butyl 3-(benzyloxycarbonylamino)-4-hydroxypyrrolidine-1-carboxylate (4.91 g, 67.1%) as an oil.

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (5:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-95344e44caf246cda2a2c633c2fadfdb
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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