HCID 86701385, compound → (2S,5R)-6-hydroxy-2-(5-(1-methylpiperidin-4-yl)-1,3,4-oxadiazol-2-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one

HRID 870838Notes

Reaction equation

HRID 870838 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[O:19][C:20]([CH:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)=[N:21][N:22]=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[O:19][C:20]([CH:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)=[N:21][N:22]=1

Participants

4

Reactant 1

HCID 86701385HCID 86701385, compound

Product 1

HCID 86701386(2S,5R)-6-hydroxy-2-(5-(1-methylpiperidin-4-yl)-1,3,4-oxadiazol-2-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-oneYield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,5R)-6-(benzyloxy)-2-(5-(1-methylpiperidin-4-yl)-1,3,4-oxadiazol-2-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one (198 mg, 0.50 mmol) in THF (20 mL) was added 10% Pd/C (200 mg). The mixture was stirred under H2 atmosphere at rt for 3 hrs. The reaction mixture was filtered and concentrated to afford (2S,5R)-6-hydroxy-2-(5-(1-methylpiperidin-4-yl)-1,3,4-oxadiazol-2-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one (151 mg, 97%), which was used directly in the next step. ESI-MS (EI+, m/z): 308.1 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-53e99b1e7ae44272897881df80a3e02c
Source dataset
uspto-grants-2015_03
Patent number
US08969570B2

Reaction notes

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