HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Cyanide → (4S,5R)-tert-butyl 5-(4-(3-(cyanomethyl)isoxazol-5-yl)phenyl)-4-(fluoromethyl)-2,2-dimethyloxazolidine-3-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Cyanide | HCID 9032 | — |
| Reactant | 18-Crown-6 | HCID 28557 | — |
| Reactant | (4S,5R)-tert-butyl 4-(fluoromethyl)-2,2-dimethyl-5-(4-(3-((methylsulfonyloxy)methyl)isoxazol-5-yl)phenyl)oxazolidine-3-carboxylate | HCID 86695496 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (4S,5R)-tert-butyl 5-(4-(3-(cyanomethyl)isoxazol-5-yl)phenyl)-4-(fluoromethyl)-2,2-dimethyloxazolidine-3-carboxylate | HCID 86713175 | 55.8% |
Reaction Steps
The product of step 1 of Example 10 (200 mg, 0.41 mmol), potassium cyanide (111 mg, 1.65 mmol), and 18-crown-6 (23 mg, 0.08 mmol) in acetonitrile (8 mL) are stirred at room temperature for 16 hours then the mixture is concentrated and purified by column chromatography on silica gel eluting with a gradient of ethyl acetate/heptane to afford the title compound (95 mg). m/z (Cl) 416 [M+H].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09206126B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-05453c7bac654ad99ea9f063de72bb05 |
| Source note | uspto-grants-2015_12 |