Sodium Bicarbonate → 8-(5-Aminopyridin-2-yl)-1,4-dioxaspiro[4,5]decane-8-carboxylic acid ethyl ester

HRID 1748505Notes

Reaction equation

HRID 1748505 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].F[B-](F)(F)F.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[CH2:29]([O:31][C:32]([C:34]1([C:44]2[CH:49]=[CH:48][C:47](Br)=[CH:46][N:45]=2)[CH2:43][CH2:42][C:37]2([O:41][CH2:40][CH2:39][O:38]2)[CH2:36][CH2:35]1)=[O:33])[CH3:30].[F-].C([N+:56](CCCC)(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:29]([O:31][C:32]([C:34]1([C:44]2[CH:49]=[CH:48][C:47]([NH2:56])=[CH:46][N:45]=2)[CH2:43][CH2:42][C:37]2([O:41][CH2:40][CH2:39][O:38]2)[CH2:36][CH2:35]1)=[O:33])[CH3:30]

Participants

8

Reactant 5

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 2733832Lithium HexamethyldisilazideHCID 44558591Tri-t-butylphosphine fluoroborateHCID 86692455HCID 86692455, compound

Product 1

HCID 866924568-(5-Aminopyridin-2-yl)-1,4-dioxaspiro[4,5]decane-8-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent2×

Procedure

1.0M Toluene-solution of lithium bis(trimethylsilyl)amide (1.89 ml) was added to bis(dibenzylideneacetone)palladium (0) (39 mg) and tri-tert-butylphosphine tetrafluoroborate (20 mg) at 70° C. under an atmosphere of nitrogen, a solution of 8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4,5]decane-8-carboxylic acid ethyl ester (500 mg) in toluene (1.4 ml) was added dropwise and stirred at the same temperature for 0.5 hours. After completion of the reaction, the reaction solution was cooled to room temperature, tetrabutylammonium fluoride (4.7 ml) was added and stirred at the same temperature for an hour. Then, a saturated aqueous solution of sodium bicarbonate was added and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give the titled compound (312 mg) as a yellow oil.

Workup

  1. customAfter completion of the reaction
  2. stirringstirred at the same temperature for an hour
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-0ebde3beb7ac4ac496e01e8582b1827b
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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