Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Borane;tetrahydrofuran | HCID 2723981 | — |
| Reactant | HCID 79117049 | HCID 79117049 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86762189 | HCID 86762189 | 92.9% |
Reaction Steps
To a stirring solution of 3-(2-fluoro-phenyl)-3-hydroxy-butyronitrile (878 mg, 4.9 mmol) in tetrahydrofuran (5 mL) was slowly added a solution of borane-tetrahydrofuran complex (12.8 mL, 12.8 mmol, 1M in tetrahydrofuran). After bubbling ceased, the reaction mixture was heated to 75° C. for 2 hours and then allowed to cool to ambient temperature and concentrated. Methanol (5 mL) was added dropwise followed by hydrogen chloride (5.4 mL, 23.8 mmol, 4N in 1,4-dioxane). The resulting mixture was heated to reflux for 2 hours, allowed to cool to ambient temperature and then concentrated at reduced pressure. The residue was triturated with ether and the precipitate was filtered, washed with ethyl acetate and air dried to give the product as a white solid (1 g, 92%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08609849B1 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-5c778ff225554786a042363c0bdf1e9a |
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| Source note | uspto-grants-2013_12 |
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