Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cyclohexane | HCID 8078 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | HCID 59599682 | HCID 59599682 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 178506019 | HCID 178506019 | 48.6% |
Reaction Steps
To a stirred solution of 1-[5-fluoro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-ylmethyl]-1,2,3,4-tetrahydroquinoline (103 mg) at room temperature in tetrahydrofuran (THF) (5 ml) under an argon atmosphere was added tetra-n-butylammonium fluoride (TBAF) (1.1 ml; 1 M solution in THF). The mixture was heated to 60° C. and stirring at that temperature was continued for 20 minutes, then the mixture was adsorbed directly on silica gel. The crude product was isolated by column chromatography (silica gel; gradient: cyclohexane→ethyl acetate) to give 1-(5-fluoro-1H-imidazol-4-ylmethyl)-1,2,3,4-tetrahydro-quinoline (32 mg) as light yellow solid. (MS (ISP): 232.1 ([M+H]+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07858652B2 |
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| Source dataset | uspto-grants-2010_12 |
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| ORD ID | ord-8e4a9d02db5b4832b069bf7568e57b78 |
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| Source note | uspto-grants-2010_12 |
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