Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tert-Butylamine | HCID 6385 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Trimethylaluminum | HCID 16682925 | — |
| Reactant | 6-[3-(3,4-Difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester | HCID 66718164 | — |
| Solvent | Heptane | HCID 8900 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 46929064 | HCID 46929064 | 13% |
Reaction Steps
A trimethylaluminium solution (2 M in toluene, 798 μL, 1.6 mmol) in dioxane (7.5 mL) was added to tert-butylamine (174 μL, 1.6 mmol) and the mixture was stirred for 1 h at 50° C. 6-[3-(3,4-Difluoro-phenyl)-5-hydroxymethyl-isoxazol-4-ylmethoxy]-nicotinic acid methyl ester (150 mg, 0.4 mmol) in dioxane (7.5 mL) was added and stirring was continued overnight at 85° C. Chromatography (silica, ethyl acetate: heptane=1:4 to 1:1) afforded the title compound (20 mg, 13%) as a colourless solid. MS: m/e=416.4 [M−H]−.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08222246B2 |
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| Source dataset | uspto-grants-2012_07 |
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| ORD ID | ord-fff4bd8e62c1404e89ba4a336a8f9880 |
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| Source note | uspto-grants-2012_07 |
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