Reaktion #588458

ord-b3d4d03aaf4f430899b14e31c6577805

Reaktionsgleichung

CC1CCCCC1
methylcyclohexane
COC(=O)[C@@H]1C[C@H]1C(=O)O
trans-cyclopropane-1,2-dicarboxylic acid monomethyl ester
C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccc(OC)cc12
quinine
→
COC(=O)[C@H]1C[C@@H]1C(=O)O
(S,S)-(+)-Cyclopropane-1,2-dicarboxylic acid monomethyl ester

Edukte

CC1CCCCC1
methylcyclohexane
COC(=O)[C@@H]1C[C@H]1C(=O)O
trans-cyclopropane-1,2-dicarboxylic acid monomethyl ester
C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccc(OC)cc12
quinine

Reagenzien

Keine

Lösungsmittel

CC(C)=O
acetone

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturHeat
  2. 2
    Sonstigethe reaction
  3. 3
    Temperaturto reflux
  4. 4
    SonstigeAfter crystallization (5 times) from acetone/methylcyclohexane
  5. 5
    Sonstigecollect 6.2 g of the diastereomeric salt (═D:+173, c:7.3 CHCl3)

Vorschrift

Add trans-cyclopropane-1,2-dicarboxylic acid monomethyl ester, Example 3a, (19.46 g) in acetone to quinine (43.8 g) In one portion. Heat the reaction to reflux, and then add methylcyclohexane (150 mL). After crystallization (5 times) from acetone/methylcyclohexane, collect 6.2 g of the diastereomeric salt (═D:+173, c:7.3 CHCl3)

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07772252B2uspto-grants-2010_08