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 1478016Notes

Reaction equation

HRID 1478016 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(Cl)Cl.[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 59.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 9-oxo-3-azaspiro[5.5]undec-7-ene-3-carboxylate (5.2 g, 19.6 mmol) in DCM (80 mL) was added 10% Pd/C (0.5 g) and the suspension was stirred under a H2 atmosphere at room temperature overnight. The reaction mixture was filtered and concentrated in vacuo, then the residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/4) to give the product as brown oil (3.1 g, 59.0%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customthe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/4)

Sources & evidence

ORD record
ord-740f0a2a9e874b0ab1c987d872863d75
Source dataset
uspto-grants-2016_08
Patent number
US09403801B2

Reaction notes

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