Diisopropylethylamine → tert-Butyl 2-(pyridin-4-yl)-2,9-diazaspiro[5.5]undecane-9-carboxylate

HRID 1253675Notes

Reaction equation

HRID 1253675 reaction equation
[CH2:1]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[CH2:5][CH2:4][CH2:3][NH:2]1.[Cl-].Cl[C:21]1[CH:26]=[CH:25][NH+:24]=[CH:23][CH:22]=1.C(N(C(C)C)C(C)C)C.C([O-])(O)=O.[Na+]>CC(O)C.C(OCC)(=O)C>[N:24]1[CH:25]=[CH:26][C:21]([N:2]2[CH2:3][CH2:4][CH2:5][C:6]3([CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]3)[CH2:1]2)=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 108772907379-35-3HCID 46912008tert-Butyl 2,9-diazaspiro(5.5)undecane-9-carboxylate

Product 1

HCID 66700745tert-Butyl 2-(pyridin-4-yl)-2,9-diazaspiro[5.5]undecane-9-carboxylate

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 2,9-diazaspiro[5.5]undecane-9-carboxylate (1 g, 3.931 mmol), 4-chloropyridinium chloride (1.765 g, 11.794 mmol) and N-ethyl-diisopropylamine (2.7 ml, 15.724 mmol) were refluxed in 2-propanol (8 ml) for 15 h, saturated NaHCO3 solution (20 ml) and ethyl acetate (8 ml) were added, the phases were separated and the aqueous phase was extracted with ethyl acetate (2×80 ml). The combined organic phases were dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica; ethyl acetate/methanol/ammonia (25 aq.) 100:10:0.25). Yield: 0.67 g (51.4%)

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate (2×80 ml)
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (silica; ethyl acetate/methanol/ammonia (25 aq.) 100:10:0.25)

Sources & evidence

ORD record
ord-1615fcdc099c48b3a50851929a76b72f
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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