Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Tetrahydro-4H-pyran-4-one | HCID 121599 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | HCID 68543319 | HCID 68543319 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 68544557 | HCID 68544557 | 94.2% |
Reaction Steps
Sodium triacetoxyborohydride (90 mg, 0.42 mmol, 2.5 equiv) was added to a mixture of 1-ethoxycarbonylmethoxy-2-methoxycarbonyl-3,8-dithia-cyclopenta[a]inden-6-yl-ammonium trifluoroacetate (85 mg, 0.17 mmol), tetrahydropyran-4-one (24 μl, 0.2 mmol, 1.2 equiv), and acetic acid (5 μl) in DCE (4 ml) and stirred at 50° C. for 17 hr. DCM (20 ml) was added and the mixture was washed with sat. NaHCO3, dried over MgSO4, filtered, and the solvent was reoved in vacuo. Purification by column chromatography yielded 72 mg (94%) of 1-ethoxycarbonylmethoxy-6-(tetrahydropyran-4-ylamino)-3,8-dithiacyclopenta[a]indene-2-carboxylic acid methyl ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07674822B2 |
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| Source dataset | uspto-grants-2010_03 |
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| ORD ID | ord-e91f40dbed9d4efbbd2fc0cbfe3ee795 |
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| Source note | uspto-grants-2010_03 |
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