Ammonia → tert-Butyl 2,9-diazaspiro(5.5)undecane-9-carboxylate

HRID 1501748Notes

Reaction equation

HRID 1501748 reaction equation
[CH:1]([C:3]1([CH2:16][CH2:17][CH3:18])[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=O.[NH3:19]>CO.[Ni]>[CH2:8]1[C:3]2([CH2:16][CH2:17][CH2:18][NH:19][CH2:1]2)[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:7]1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 58017246Tert-butyl 4-formyl-4-propylpiperidine-1-carboxylate

Product 1

HCID 46912008tert-Butyl 2,9-diazaspiro(5.5)undecane-9-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 935NickelSolvent

Conditions

Temperature
110 °C

Procedure

Tert-butyl 4-formyl-4-propylpiperidinecarboxylate (30 g) was dissolved in a saturated solution of ammonia in methanol, and 15 g of Raney Ni was added. The reaction mixture was heated to 110° C. at 80 atmospheres pressure in a 2 L high-pressure autoclave. The mixture was filtered to remove the catalyst and the filtrate was concentrated to give residue which was purified by column chromatography to afford tert-butyl 3,8-diazaspiro[5,5]undecane-3-carboxylate.

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. customto remove the catalyst
  4. concentrationthe filtrate was concentrated
  5. customto give residue which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-2fbb5d32ef3d4744b23c982931c242ce
Source dataset
uspto-grants-2015_12
Patent number
US09206198B2

Reaction notes

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