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

HRID 1689511Notes

Reaction equation

HRID 1689511 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-bd51db246643472fbb66b587160a081b
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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