Tert-butyl 9-oxo-3-azaspiro[5.5]undec-7-ene-3-carboxylate → tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate

HRID 2059915Notes

Reaction equation

HRID 2059915 reaction equation
[O:1]=[C:2]1[CH2:19][CH2:18][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH:4]=[CH:3]1>C(O)C.[Pd]>[O:1]=[C:2]1[CH2:19][CH2:18][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 59311817Tert-butyl 9-oxo-3-azaspiro[5.5]undec-7-ene-3-carboxylate

Product 1

HCID 51072194tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylateYield 38%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

tert-Butyl 9-oxo-3-azaspiro[5.5]undec-7-ene-3-carboxylate (6.41 mmol, 1 eq) was taken up in ethanol (500 ml) and to the mixture was added 10% Pd/C (3.4 g). The mixture was hydrogenated at 25° C. for 16 h. The reaction mixture was filtered through celite, concentrated and purified by silica gel column chromatography to yield the desired product. Yield: 38%

Workup

  1. filtrationThe reaction mixture was filtered through celite,
  2. concentrationconcentrated
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-8b3c1197f4d04759adb66fb5eb89eb16
Source dataset
uspto-grants-2012_10
Patent number
US08278319B2

Reaction notes

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