Water → HCID 86692455, compound

HRID 1748504Notes

Reaction equation

HRID 1748504 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:15][CH2:14][C:9]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Br:26][C:27]1[CH:28]=[CH:29][C:30](F)=[N:31][CH:32]=1.O>O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1([C:30]2[CH:29]=[CH:28][C:27]([Br:26])=[CH:32][N:31]=2)[CH2:15][CH2:14][C:9]2([O:10][CH2:11][CH2:12][O:13]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 2733832Lithium HexamethyldisilazideHCID 27831685-Bromo-2-fluoropyridineHCID 10488810Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylate

Product 1

HCID 86692455HCID 86692455, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

A solution of 1,4-dioxaspiro[4,5]decane-8-carboxylic acid ethyl ester (6.09 g) in tetrahydrofuran (14 ml) was added dropwise to a tetrahydrofuran solution (32 ml) of 1.0M tetrahydrofuran solution of lithium bis(trimethylsilyl)amide (39.8 ml) at −78° C., and stirred at the same temperature for 1.5 hours. Next, a solution of 5-bromo-2-fluoropyridine (5.0 g) in tetrahydrofuran (14 ml) was added dropwise and stirred at the same temperature for 0.5 hour and at room temperature for an hour. After completion of the reaction, water was added to the reaction solution and extracted with ethyl acetate twice. 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 8-(5-bromopyridin-2-yl)-1,4-dioxaspiro[4,5]decane-8-carboxylic acid ethyl ester (6.9 g) as a colorless oil.

Workup

  1. stirringstirred at the same temperature for 0.5 hour and at room temperature for an hour
  2. additionwas added to the reaction solution
  3. extractionextracted with ethyl acetate twice
  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-a47aaa2c2c6e4fc89a3700233c86cbca
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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