(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

HRID 870824Notes

Reaction equation

HRID 870824 reaction equation
C([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]1[CH:22]=[CH:21][O:20][N:19]=1)C1C=CC=CC=1>C1COCC1.[Pd]>[OH:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]1[CH:22]=[CH:21][O:20][N:19]=1

Participants

4

Reactant 1

HCID 86701372(2S,5R)-6-(benzyloxy)-2-(isoxazol-3-yl)-1,6-diazabicyclo[3.2.1]octan-7-one

Product 1

HCID 86701373(2S,5R)-6-hydroxy-2-(isoxazol-3-yl)-1,6-diazabicyclo[3.2.1]octan-7-oneYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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]+.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated
  3. washThe residue was washed with Et2O (3×)
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-8f20bde8850f48408733639087eff7dc
Source dataset
uspto-grants-2015_03
Patent number
US08969570B2

Reaction notes

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