HuagongsheHuagongshe Chemistry Print Report · For research reference only
Isopropanol heptane → (2R,4S)-Methyl 2-(3,3-dimethylbutyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Isopropanol heptane | HCID 21225753 | — |
| Reactant | trans-Methyl 2-(3,3-dimethylbutyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate | HCID 131730456 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (2R,4S)-Methyl 2-(3,3-dimethylbutyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate | HCID 66732587 | 43% |
Reaction Steps
Trans-methyl 2-(3,3-dimethylbutyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)piperidine-1-carboxylate (194 mg, 0.63 mmol) was subjected to chiral preparative HPLC (Column: Chiralpak IC (250×20), 5 μm particle size, mobile phase: Heptane/IPA 85/15, flow rate 18 mL/min) to yield (2R,4S)-methyl 2-(3,3-dimethylbutyl)-4-(3-oxo-2,3-dihydroisoxazol-5-yl)-piperidine-1-carboxylate (83 mg, 43%), Chiral purity 99.3% ee, Optical rotation [α]D20=−12.3 (acetonitrile, c=1)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08415378B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-cc8ad5f866b84dacb3e4170160ab15b1 |
| Source note | uspto-grants-2013_04 |