Methylcyclohexane → (1S,2S)-2-methoxycarbonylcyclopropanecarboxylic acid
Reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:7][C@H:6]1[C:8]([OH:10])=[O:9])=[O:4].COC1C=CC2N=CC=C([C@@H](O)[C@H]3N4C[C@H](C=C)[C@@H](CC4)C3)C=2C=1.CC1CCCCC1>CC(C)=O>[CH3:1][O:2][C:3]([C@H:5]1[CH2:7][C@@H:6]1[C:8]([OH:10])=[O:9])=[O:4]Participants
5
Procedure
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 (αD:+173, c:7.3 CHCl3)
Workup
- temperatureHeat
- customthe reaction
- temperatureto reflux
- customAfter crystallization (5 times) from acetone/methylcyclohexane
- customcollect 6.2 g of the diastereomeric salt (αD:+173, c:7.3 CHCl3)
Sources & evidence
- ORD record
- ord-cab5625791944481b134ae2d9921a211
- Source dataset
- uspto-grants-2007_03
- Patent number
- US07186724B2
Reaction notes
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