2-Methylpyridine → HCID 59651881, compound

HRID 2042574Notes

Reaction equation

HRID 2042574 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](OCC)=[O:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([C:21](=[O:22])[CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 79752-MethylpyridineHCID 2733832Lithium HexamethyldisilazideHCID 11783050ethyl 4-(1-t-butoxycarbonyl-4-piperidyloxy)benzoate

Product 1

HCID 59651881HCID 59651881, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

A solution of 4-(4-ethoxycarbonylphenoxy)piperidine-1-carboxylic acid tert-butyl ester (3.5 g, 10 mmol) and 2-methylpyridine (1.9 g, 2.0 mmol) in 50 mL of THF was stirred at 0° C. as LiHMDS (1.0M, 22 mL) was added dropwise. The reaction was stirred at 45° C. overnight, then quenched with ice-water and the solvent evaporated. The residue was extracted with CH2Cl2 (3×30 mL), and the combined CH2Cl2 layers were washed with saturated NaHCO3, saturated NaCl solution, dried over Na2SO4, and concentrated to give the product; Mp 138-140° C.; MS m/z 397 (M+H).

Workup

  1. additionwas added dropwise
  2. customquenched with ice-water
  3. customthe solvent evaporated
  4. extractionThe residue was extracted with CH2Cl2 (3×30 mL)
  5. washthe combined CH2Cl2 layers were washed with saturated NaHCO3, saturated NaCl solution
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto give the product

Sources & evidence

ORD record
ord-62d8149bdbd344969c36f688f95792a4
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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