Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium formate | HCID 2723923 | — |
| Reactant | HCID 58400514 | HCID 58400514 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 58400517 | HCID 58400517 | 64% |
Reaction Steps
A 75:25 diastereoisomeric mixture of 6-fluoro-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2H-chromene (50 mg, 0.18 mmol, 90.4% A) was dissolved in ethanol and stirred under nitrogen atmosphere at 25° C. Ammonium formate (60.5 mg, 0.96 mmol) and 10% palladium on carbon (50 mg) were added to the stirred solution and the reaction mixture refluxed for 15 h. The reaction mixture was checked to show complete conversion of the starting material. The solids were removed by filtration and the filtrate was concentrated under reduced pressure to furnish 6-fluoro-3,4-dihydro-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2H-chromene (40 mg, 0.115 mmol, 72.6% A, 64% yield) as a 75:25 mixture of diastereoisomers.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08258323B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-bcc31dbd1f60421ab3f6c5be98ea10c7 |
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| Source note | uspto-grants-2012_09 |
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