Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | tert-Butyldimethylsilyl trifluoromethanesulphonate | HCID 123564 | — |
| Reactant | Ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate | HCID 565357 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66727759 | HCID 66727759 | — |
Reaction Steps
To a solution of (1RS,5SR,6RS)-2-oxo-bicyclo[3,1,0]hexane-6-carboxylic acid ethyl ester (28.93 g, 172 mmole) in dichloromethane (430 ml) was added at 22° C. NEt3 (36.0 ml, 258 mmole), the mixture was cooled to 0° C. and treated with tert-butyldimethylsilyl triflate (43.5 ml, 189.2 mmole) keeping the temperature below 10° C. The mixture was allowed to warm to 22° C. over 2 h, washed with saturated aqueous NaHCO3, the organic layer was dried, evaporated and the residue purified over aluminiumoxide (100 g) using cyclohexane/AcOEt (9:1) to give the title compound as a yellow oil which was used without further purification in the next step.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08815881B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-f5efdb3012f949adb2b7ef234d134c81 |
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| Source note | uspto-grants-2014_08 |
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