Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Chloromethyl Methyl Ether | HCID 7864 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | HCID 89962749 | HCID 89962749 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 89963478 | HCID 89963478 | 62% |
Reaction Steps
To a solution of the (1S*,2R*,4S*)-4-benzyloxy-2-(1-methyl-1H-pyrazol-5-yl)cyclopentanol (350 mg, 1.29 mmol) prepared in Example 98a and diisopropylethylamine (1.3 mL, 7.64 mmol) in dichloromethane (5.0 mL), chloromethyl methyl ether (0.48 mL, 6.32 mmol) was added, and the reaction solution was stirred at 40° C. for 5 hours. After allowing to cool, water (10 mL) was added to the reaction solution, and an organic layer was extracted. The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=1:2) to yield the title compound (250 mg, 62%) as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08889741B2 |
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| Source dataset | uspto-grants-2014_11 |
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| ORD ID | ord-026ec30f89cf4f5aa2dda761e68fe1ea |
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| Source note | uspto-grants-2014_11 |
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