Benzyl 2,5-dioxopyrrolidine-1-carboxylate → trans-Benzyl 3-hydroxycyclopentylcarbamate

HRID 271370Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271370
[OH:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([NH2:7])[CH2:3]1.[CH2:8]([O:15][C:16](N1C(=O)CCC1=O)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(#N)C>[OH:1][C@H:2]1[CH2:6][CH2:5][C@H:4]([NH:7][C:16](=[O:17])[O:15][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:3]1

Komponenten

4

Edukt 2

HCID 3826287Benzyl 2,5-dioxopyrrolidine-1-carboxylateHCID 42614395(1S,3S)-3-Aminocyclopentan-1-ol

Produkt 1

HCID 59834849trans-Benzyl 3-hydroxycyclopentylcarbamateAusbeute 981,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of crude trans-3-hydroxycyclopentanamine (0.42 g, 4.2 mmol) and N-(benzyloxycarbonyl)succinimide (1.05 g, 0.42 mmol) in acetonitrile (40 ml) was stirred at ambient temperature under nitrogen for 18 hours. The mixture was concentrated under reduced pressure. The residue was taken up in ethyl acetate (150 ml), washed with water (3×75 ml), and brine (50 ml), dried (sodium sulfate), filtered, and the solvent evaporated under reduced pressure to give benzyl (trans-3-hydroxycyclopentyl)carbamate (0.97 g, 98%), as a white solid.

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. washwashed with water (3×75 ml), and brine (50 ml)
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fb46d788fc814cb2ad333ca1dcf47da3
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452893B2

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