Ammonium formate → 9-(tert-Butyl) 2-methyl 1-oxa-4,9-diazaspiro[5.5]undecane-2,9-dicarboxylate

HRID 72873Notes

Reaction equation

HRID 72873 reaction equation
C([N:8]1[CH2:13][C:12]2([CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[O:11][CH:10]([C:26]([O:28][CH3:29])=[O:27])[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CCO.[Pd]>[O:11]1[C:12]2([CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH2:13][NH:8][CH2:9][CH:10]1[C:26]([O:28][CH3:29])=[O:27]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68292133HCID 68292133, compound

Product 1

HCID 682918779-(tert-Butyl) 2-methyl 1-oxa-4,9-diazaspiro[5.5]undecane-2,9-dicarboxylateYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 9-tert-butyl 2-methyl 4-benzyl-1-oxa-4,9-diazaspiro[5.5]undecane-2,9-dicarboxylate (670 mg, 1.66 mmol), ammonium formate (623 mg, 9.936 mmol) and palladium, 10 wt. % on activated carbon (353 mg, 3.31 mmol) in EtOH (5 mL) was heated at 65° C. for 50 minutes. The reaction mixture was cooled to room temperature, filtered and partitioned between EtOAc/1M aq. NaOH. The layers were separated and the organic layer was dried over Na2SO4, filtered and concentrated in vacuo to yield 9-tert-butyl 2-methyl 1-oxa-4,9-diazaspiro[5.5]undecane-2,9-dicarboxylate as a foam (386 mg, 74%). ESI-MS m/z calc. 314.2. Found 315.5 (M+1); Retention time: 0.99 minutes (3 min run).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. custompartitioned between EtOAc/1M aq. NaOH
  4. customThe layers were separated
  5. dry with materialthe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-71f43f1d2536418c82f2481213db621e
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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