Methylcyclohexane → (1S,2S)-2-methoxycarbonylcyclopropanecarboxylic acid

HRID 1986959Notes

Reaction equation

HRID 1986959 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

Reactant 3

HCID 7962MethylcyclohexaneHCID 3034034QuinineHCID 12510972rac-(1R,2R)-2-(methoxycarbonyl)cyclopropane-1-carboxylic acid

Product 1

HCID 11708069(1S,2S)-2-methoxycarbonylcyclopropanecarboxylic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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

  1. temperatureHeat
  2. customthe reaction
  3. temperatureto reflux
  4. customAfter crystallization (5 times) from acetone/methylcyclohexane
  5. customcollect 6.2 g of the diastereomeric salt (αD: +173, c: 7.3 CHCl3)

Sources & evidence

ORD record
ord-720001fae95a4b9bb15c5c72cae92664
Source dataset
uspto-grants-2009_06
Patent number
US07550469B2

Reaction notes

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