Methyl iodide → HCID 67536157, compound

HRID 2236160Notes

Reaction equation

HRID 2236160 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11]2)=[N:8][CH:9]=1)([O-:3])=[O:2].[H-].[Na+].I[CH3:19]>CN(C=O)C>[CH3:19][O:15][CH:12]1[CH2:13][CH2:14][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=2)[CH2:11]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 62916798HCID 62916798, compound

Product 1

HCID 67536157HCID 67536157, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 1-(5-nitro-pyridin-2-yl)-pyrrolidin-3-ol (120 mg, 0.57 mmol) in 5 mL of DMF was added 10 equivalent of sodium hydride (228 mg, 5.7 mmol, 60% in mineral oil). The mixture was stirred at 23° C. for 15 min followed by the addition of 10 equivalent of iodomethane (355 uL, 5.7 mmol). The reaction was continually stirred for 2 h and then extracted with ethyl acetate and water. The organic phase was dried and solvent was evaporated. The residue was purified on a flash chromatography column with EtOAc/hexanes to afford 2-(3-methoxy-pyrrolidin-1-yl)-5-nitro-pyridine. LRMS calcd for C10H13N3O3 (m/e) 223, obsd 224 (M+H).

Workup

  1. stirringThe reaction was continually stirred for 2 h
  2. extractionextracted with ethyl acetate and water
  3. customThe organic phase was dried
  4. customsolvent was evaporated
  5. customThe residue was purified on a flash chromatography column with EtOAc/hexanes

Sources & evidence

ORD record
ord-06dba073cc114fbf8e982e37d60639cb
Source dataset
uspto-grants-2010_05
Patent number
US07714126B2

Reaction notes

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