Triethylamine → tert-Butyl 9-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate

HRID 1808352Notes

Reaction equation

HRID 1808352 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].Cl[C:21]1[CH:26]=[CH:25][NH+:24]=[CH:23][CH:22]=1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(O)CCC.C(OCC)(=O)C>[N:24]1[CH:25]=[CH:26][C:21]([N:16]2[CH2:17][CH2:18][C:11]3([CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]3)[CH2:14][CH2:15]2)=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 108772907379-35-3HCID 15296367tert-Butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 59486425tert-Butyl 9-(pyridin-4-yl)-3,9-diazaspiro[5.5]undecane-3-carboxylate

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl-3,9-diazaspiro[5.5]undecane-3-carboxylate (1 g, 3.931 mmol), 4-chloro-pyridinium chloride (1.765 g, 11.794 mmol) and triethylamine (2.2 ml, 15.725 mmol) were refluxed for 15 h in 1-butanol (50 ml). Saturated sodium hydrogen carbonate solution (30 ml) and ethyl acetate (80 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 magnesium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (silica gel, ethyl acetate/-hexane/methanol/ammonia (25% aq.), 400:40:40:1). Yield: 0.52 g (39%)

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 magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (silica gel, ethyl acetate/-hexane/methanol/ammonia (25% aq.), 400:40:40:1)

Sources & evidence

ORD record
ord-d4cb713269a944a9bcc27e98c734133b
Source dataset
uspto-grants-2013_01
Patent number
US08357717B2

Reaction notes

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