Methyl iodide → HCID 22629553, compound

HRID 238259Notes

Reaction equation

HRID 238259 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([OH:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:23]I>C1COCC1.[Cl-].[Na+].O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([O:20][CH3:23])([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11231242Tert-butyl 4-hydroxy-4-phenylpiperidine-1-carboxylate

Product 1

HCID 22629553HCID 22629553, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

4-Hydroxy-4-phenyl-piperidine-1-carboxylic acid tert-butyl ester (0.5 g, 1.8 mmol) was dissolved in dry THF (15 mL) and sodium hydride (60% disp. in mineral oil; 0.076 g, 1.9 mmol) added and the mixture stirred for 1 hour. Methyl iodide (0.16 mL; 2.7 mmol) was then added and the mixture stirred overnight. Brine was added and the product extracted into ethyl acetate, dried over sodium sulphate, filtered and the solvent removed by evaporation. The residue was purified by flash chromatography on silica eluting with 0-10% ethyl acetate/hexane. The fractions containing the desired product were concentrated under vacuum to give the title compound as a clear colourless oil (0.35 g).

Workup

  1. stirringthe mixture stirred overnight
  2. extractionthe product extracted into ethyl acetate
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent removed by evaporation
  6. customThe residue was purified by flash chromatography on silica eluting with 0-10% ethyl acetate/hexane
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-171249ee4d344d4eb6f7122c13e0c164
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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