HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methylcyclohexane → (1S,2S)-2-methoxycarbonylcyclopropanecarboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methylcyclohexane | HCID 7962 | — |
| Reactant | Quinine | HCID 3034034 | — |
| Reactant | rac-(1R,2R)-2-(methoxycarbonyl)cyclopropane-1-carboxylic acid | HCID 12510972 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | (1S,2S)-2-methoxycarbonylcyclopropanecarboxylic acid | HCID 11708069 | — |
Reaction Steps
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)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07521445B2 |
| Source dataset | uspto-grants-2009_04 |
| ORD ID | ord-2cc9999e42444285a321c4af10808e39 |
| Source note | uspto-grants-2009_04 |