Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | HCID 52914598 | HCID 52914598 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 52914599 | HCID 52914599 | 99.4% |
Reaction Steps
To a solution of Acetic acid (5S,6S,7R,8S)-7,8-diacetoxy-5-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-4-oxa-spiro[2.5]oct-6-yl ester (300 mg, 0.56 mmole) in dry dichloromethane (5 mL), BBr3 (0.54 mL, 5.6 mmole) was added at −78° C. and stirred at −15° C. for 1 hour. The reaction mixture was diluted with diethyl ether (5.0 mL), stirred for 30 min. and further diluted with water (15 mL) and extracted with DCM (2×50 mL) to furnish 280 mg of Acetic acid (5S,6S,7R,8S)-7,8-diacetoxy-5-[4-chloro-3-(4-hydroxy-benzyl)-phenyl]-4-oxa-spiro[2.5]oct-6-yl ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08394772B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-79c94ac951494255bf879476874087e1 |
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| Source note | uspto-grants-2013_03 |
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