HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → (2S,4S)-Methyl 2-(4-fluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | trans-Methyl 2-(4-fluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate | HCID 131730459 | — |
| Solvent | Carbon Dioxide | HCID 280 | — |
| Product | (2S,4S)-Methyl 2-(4-fluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate | HCID 66739000 | 30.3% |
Reaction Steps
Trans-methyl 2-(4-fluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (0.268 g, 0.8 mmol) was subjected to chiral preparative HPLC (Column: Chiralcel OJ (250×30), 5 μm particle size, mobile phase: 10% EtOH in CO2 (175 bar), flow rate 150 mL/min) to yield (2S,4S)-methyl 2-(4-fluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)-piperidine-1-carboxylate (81 mg, 30%), Chiral purity 99.8% ee, Optical rotation [α]D20=+29.3 (acetonitrile, c=1)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08415378B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-4e65de0dc4c14ba18a7ead270b55f7c1 |
| Source note | uspto-grants-2013_04 |