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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 515597Generated: October 31, 2026

(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

https://huagongshe.com/reaction/515597

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(2S,5R)-6-(benzyloxy)-2-(isoxazol-3-yl)-1,6-diazabicyclo[3.2.1]octan-7-oneHCID 86701372—
CatalystPalladiumHCID 23938—
SolventTetrahydrofuranHCID 8028—
Product(2S,5R)-6-hydroxy-2-(isoxazol-3-yl)-1,6-diazabicyclo[3.2.1]octan-7-oneHCID 8670137398%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09108966B2
Source datasetuspto-grants-2015_08
ORD IDord-37205429af4f43ae9a3fdf3b58d911f4
Source noteuspto-grants-2015_08