Methyl iodide → HCID 18423446, compound

HRID 1282013Notes

Reaction equation

HRID 1282013 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][C:17]([OH:20])([CH3:19])[CH3:18])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:21]I>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH2:16][C:17]([O:20][CH3:21])([CH3:19])[CH3:18])[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18423490358625-61-3

Product 1

HCID 18423446HCID 18423446, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 0.06 g (2.5 mmol) of NaH in 5 mL of DMF at rt was added a solution of 0.1 g (0.39 mmol) of 1-t-butoxycarbonyl-4-(2-hydroxy-2-methyl-1-propyl)piperidine in 3 mL of DMF. After stirring for 20 min, 0.22 mL (3.5 mmol) of CH3I was added to the reaction mixture and the reaction mixture was stirred for 2 h. The reaction mixture was quenched with water and extracted with EtOAc. The combined organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes:ethyl acetate, 9:1) to give 0.096 g of the title compound.

Workup

  1. stirringthe reaction mixture was stirred for 2 h
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with EtOAc
  4. washThe combined organic fractions were washed with sat'd NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by chromatography (silica, hexanes:ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-a556bcf4eb524dec9f2bdb1ac6ce5fb4
Source dataset
uspto-grants-2002_09
Patent number
US06455548B2

Reaction notes

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