Dicyclohexylcarbodiimide → 8-Benzyl-3-oxa-8-azabicyclo[3.2.1]octane-2,4-dione

HRID 1743698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1743698
[CH2:1]([N:8]1[C@H:12]([C:13]([OH:15])=O)[CH2:11][CH2:10][C@@H:9]1[C:16]([OH:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[CH2:1]([N:8]1[CH:9]2[CH2:10][CH2:11][CH:12]1[C:13](=[O:15])[O:18][C:16]2=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 10868DicyclohexylcarbodiimideHCID 26202186rac-(2R,5S)-1-benzylpyrrolidine-2,5-dicarboxylic acid

Produkt 1

HCID 222355968-Benzyl-3-oxa-8-azabicyclo[3.2.1]octane-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of cis-1-benzyl-2,5-pyrrolidinedicarboxylic acid (60 g, 0.24 mol; from Preparation A, step (c) above) and dicyclohexylcarbodiimide (49.7 g, 0.24 mol) in THF (1.2 L) was heated at reflux for 18 hours. The reaction was cooled and filtered to remove the urea by-product. The filtrate was concentrated in vacuo to afford a dark brown viscous oil which was used in the next step without further purification.

Aufarbeitung

  1. temperatureat reflux for 18 hours
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. customto remove the urea by-product
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto afford a dark brown viscous oil which
  7. customwas used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-f7984d0f1a1c48c9b6f1dc53df2c21e7
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07012074B2

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