HCID 57423794, compound → HCID 57986798, compound

HRID 871907Notes

Reaction equation

HRID 871907 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[S:15][C:16]([CH3:21])=[C:17]([CH:19]=[O:20])[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][Mg]I>C1COCC1.CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[S:15][C:16]([CH3:21])=[C:17]([CH:19]([OH:20])[CH3:22])[N:18]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 57423794HCID 57423794, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 57986798HCID 57986798, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(4-formyl-5-methyl-thiazol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.31 g, 1 mmol) in THF (10 mL) was added MeMgI (1 mL, 3 mmol) in Et2O at room temperature. The resulting mixture was stirred at room temperature for 1 hour. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic layer was washed with H2O and brine. After drying over Na2SO4, the solvent was removed. The residue was purified by flash chromatography on silica gel to afford the desired product.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with H2O and brine
  4. dry with materialAfter drying over Na2SO4
  5. customthe solvent was removed
  6. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-75abb2e4523f45f086fcbbdf3faac804
Source dataset
uspto-grants-2015_03
Patent number
US08975258B2

Reaction notes

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