Methyl iodide → HCID 51354610, compound

HRID 2367636Notes

Reaction equation

HRID 2367636 reaction equation
C[C:2]([N:5]([C@@H:9]1[CH2:14][C@@H:13]([CH3:15])[CH2:12][N:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10]1)[C:6](=[O:8])[O-:7])(C)C.[H-].[Na+].CI.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:2][N:5]([C@@H:9]1[CH2:14][C@@H:13]([CH3:15])[CH2:12][N:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10]1)[C:6](=[O:8])[O:7][C:13]([CH3:15])([CH3:14])[CH3:12]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 86659202HCID 86659202, compound

Product 1

HCID 51354610HCID 51354610, compoundYield 158%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1,1-dimethylethyl[(3R,5R)-5-methyl-1-(phenylmethyl)-3-piperidinyl]carbamate (196 mg, 0.644 mmol) in DMF (3 mL) was added NaH (38.6 mg, 0.966 mmol), and the resulting mixture was vigorously stirred for 30 minutes. CH3I (0.044 mL, 0.708 mmol) was added, and the reaction mixture was stirred for 3 hours at room temperature. Saturated aqueous NaHCO3 was added carefully (˜5 mL: initial vigorous bubbling), and the resulting mixture was poured onto water and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated. Flash chromatography on SiO2 (gradient: 100% Hexane to 30% EtOAc/Hexane) afforded the title compound (162 mg) as a colorless oil. LC-MS (ES) m/z=319 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred for 3 hours at room temperature
  2. custominitial vigorous bubbling), and the resulting mixture
  3. additionwas poured onto water and EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d217cbe5cb87404290c74afcc5386c3c
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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