Pyridazine → HCID 57803299, compound

HRID 1025770Notes

Reaction equation

HRID 1025770 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][N:2]=1.CC1CCCN(C)C1(C)C.[Li].[O:18]1[C:22]2([CH2:27][CH2:26][C:25](=[O:28])[CH2:24][CH2:23]2)[O:21][CH2:20][CH2:19]1>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:25]2([OH:28])[CH2:26][CH2:27][C:22]3([O:21][CH2:20][CH2:19][O:18]3)[CH2:23][CH2:24]2)[N:2]=1

Participants

5

Reactant 3

HCID 9259PyridazineHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 66701855Lithium tetramethylpiperidine

Product 1

HCID 57803299HCID 57803299, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of pyridazine (17.7 mmol, 1.28 mL) in THF (60 mL) was added 2,2,6,6, lithium tetramethylpiperidine (71 mmol, 10 g) at −78° C. The reaction was then stirred for 6 min and 1,4-dioxa-spiro[4.5]decan-8-one (71 mmol, 11 g) was added. The reaction was stirred for 5 h at −78° C. at which point the reaction was quenched using a solution of ethanol, hydrochloric acid and THF (30 mL, 1:1:1). The reaction was allowed to warm to ambient temperature and the reaction mixture was extracted using EtOAc. The organic layers were combined and dried over MgSO4. The residue was then purified using flash chromatography to afford the desired alcohol (44%, 1.84 g). MS [M+H]+ 237.1.

Workup

  1. stirringThe reaction was stirred for 5 h at −78° C. at which
  2. customwas quenched
  3. extractionthe reaction mixture was extracted
  4. dry with materialdried over MgSO4
  5. customThe residue was then purified

Sources & evidence

ORD record
ord-4f7580e692524caaa9e850a7dbbe4397
Source dataset
uspto-grants-2014_05
Patent number
US08729063B2

Reaction notes

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