Ammonium formate → Tert-butyl 2,2-dimethyl-1-oxa-4,9-diazaspiro[5.5]undecane-4-carboxylate

HRID 471282Notes

Reaction equation

HRID 471282 reaction equation
C([N:8]1[CH2:27][CH2:26][C:11]2([O:16][C:15]([CH3:18])([CH3:17])[CH2:14][N:13]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:12]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:17][C:15]1([CH3:18])[CH2:14][N:13]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[CH2:12][C:11]2([CH2:26][CH2:27][NH:8][CH2:9][CH2:10]2)[O:16]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 57989295Tert-butyl 9-benzyl-2,2-dimethyl-1-oxa-4,9-diazaspiro[5.5]undecane-4-carboxylate

Product 1

HCID 57989209Tert-butyl 2,2-dimethyl-1-oxa-4,9-diazaspiro[5.5]undecane-4-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 9-benzyl-2,2-dimethyl-1-oxa-4,9-diazaspiro[5.5]undecane-4-carboxylate (Example 271, step b) (0.8 g) dissolved in ethanol (50 mL) and 10% palladium on carbon (0.5 g) was treated with ammonium formate (0.8 g) and the reaction mixture heated at reflux for 30 minutes. The mixture was cooled to room temperature and filtered through diatomacious earth. The solvent was evaporated and the residue azeotroped with acetonitrile (×2) to afford the subtitled compound. Yield 0.55 g.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 30 minutes
  3. filtrationfiltered through diatomacious earth
  4. customThe solvent was evaporated
  5. customthe residue azeotroped with acetonitrile (×2)

Sources & evidence

ORD record
ord-710273b9b1a047ce89c478e8dc69b4fb
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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