Methyl iodide → HCID 86657828, compound

HRID 1972068Notes

Reaction equation

HRID 1972068 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([CH2:15][N:16]=[N+:17]=[N-:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:22]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH3:22])[CH:10]([CH2:15][N:16]=[N+:17]=[N-:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 72447677HCID 72447677, compound

Product 1

HCID 86657828HCID 86657828, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3-azidomethyl-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (2 mmol, 0.512 g; Example 100) in DMF (5 mL) at 0° C. was added NaH (0.1 g, 60% dispersion in mineral oil) and continued stirring at 0° C. for 20 min. To this was Iodomethane (0.5 mL) and stirred at room temperature for 20 min. The volatiles were removed under reduced pressure, residue was dissolved in ethyl acetate (10 mL), washed with water, separated the organic layer, dried and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography to get 3-azidomethyl-4-methoxy-piperidine-1-carboxylic acid tert-butyl ester (0.41 g, 76% yield).

Workup

  1. customThe volatiles were removed under reduced pressure, residue
  2. dissolutionwas dissolved in ethyl acetate (10 mL)
  3. washwashed with water
  4. customseparated the organic layer
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash silica gel column chromatography

Sources & evidence

ORD record
ord-fafd34958d7e44eb82c398b7da739806
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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