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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 1253717
Notes
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Reaction equation

HRID 1253717 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>CO.[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A solution of tert-butyl 9-oxo-3-azaspiro[5.5]undec-7-ene-3-carboxylate (15.09 mmol, 1.0 eq.) in MeOH (40 ml) was degassed with argon for 15 min and then Pd—C (1.0 g) was added. The reaction mixture was stirred under H2 balloon pressure at 25° C. for 16 h. The mixture was filtered through celite and filtrate concentrated to give the desired product as a light yellow sticky solid. Yield: >99%

Workup

  1. filtrationThe mixture was filtered through celite and filtrate
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a619d205099e41ea96b34ac98e928a9d
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08455475B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes