HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → (2S,4S)-methyl 2-(3-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-(3-fluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate | HCID 131730462 | — |
| Solvent | Carbon Dioxide | HCID 280 | — |
| Product | (2S,4S)-methyl 2-(3-fluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate | HCID 68498619 | 38.5% |
Reaction Steps
Trans-methyl 2-(3-fluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (214 mg, 0.64 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-(3-fluorobenzyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate 77 mg (38.5%), Chiral purity 99.6% ee, Optical rotation [α]D20=+64.9 (acetonitrile, c=1)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08415378B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-867010f9e57c4247afaf5e9203c1195e |
| Source note | uspto-grants-2013_04 |