HuagongsheHuagongshe Chemistry Print Report · For research reference only
(2S,5R)-6-(benzyloxy)-2-(isoxazol-3-yl)-1,6-diazabicyclo[3.2.1]octan-7-one → (2S,5R)-6-hydroxy-2-(isoxazol-3-yl)-1,6-diazabicyclo[3.2.1]octan-7-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (2S,5R)-6-(benzyloxy)-2-(isoxazol-3-yl)-1,6-diazabicyclo[3.2.1]octan-7-one | HCID 86701372 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (2S,5R)-6-hydroxy-2-(isoxazol-3-yl)-1,6-diazabicyclo[3.2.1]octan-7-one | HCID 86701373 | 98% |
Reaction Steps
A mixture of (2S,5R)-6-(benzyloxy)-2-(isoxazol-3-yl)-1,6-diazabicyclo[3.2.1]octan-7-one (196 mg, 0.656 mmol) and 10% Pd/C (80 mg) in THF (20 mL) was stirred at rt for 1.5 h under H2. The reaction mixture was then filtered and concentrated. The residue was washed with Et2O (3×) and dried under high vacuum to afford (2S,5R)-6-hydroxy-2-(isoxazol-3-yl)-1,6-diazabicyclo[3.2.1]octan-7-one (130 mg, 98%), which was in the next step directly. ESI-MS (EI+, m/z): 210 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09108966B2 |
| Source dataset | uspto-grants-2015_08 |
| ORD ID | ord-37205429af4f43ae9a3fdf3b58d911f4 |
| Source note | uspto-grants-2015_08 |