Trifluoroacetic acid → HCID 89923929, compound

HRID 1500924Notes

Reaction equation

HRID 1500924 reaction equation
C([N:8]1[CH2:15][CH:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:13][C:9]21[CH2:12][O:11][CH2:10]2)C1C=CC=CC=1.C(O)(C(F)(F)F)=O>CCO.[OH-].[OH-].[Pd+2]>[CH2:10]1[C:9]2([CH2:13][CH:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:15][NH:8]2)[CH2:12][O:11]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89923975HCID 89923975, compound

Product 1

HCID 89923929HCID 89923929, compoundYield 105.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 5-benzyl-2-oxa-5-azaspiro[3.4]octane-7-carboxylate (550 mg, 2.00 mmol) in 30 mL of EtOH was stirred with 10% Pd(OH)2/C(105 mg) in the presence of TFA (20 μL) at room temperature overnight. The resulting mixture was concentrated in vacuo. The residue was dissolved in 20 mL of DCM and washed with saturated Na2CO3 (20 mL). The organic layer was dried over Na2SO4 and then concentrated in vacuo to afford ethyl 2-oxa-5-azaspiro[3.4]octane-7-carboxylate (390 mg, yield: 100%) as viscous oil.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in 20 mL of DCM
  3. washwashed with saturated Na2CO3 (20 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6cec6bb5995547638f8b7f4ee9b23238
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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