Methyl iodide → 4-Benzyl-5-bromo-2-[(3r,4r)-3-hydroxy-4-methoxypyrrolidine-1-yl]pyridine

HRID 1359397Notes

Reaction equation

HRID 1359397 reaction equation
[H-].[Na+].[CH3:3]I.[CH2:5]([C:12]1[C:17]([Br:18])=[CH:16][N:15]=[C:14]([N:19]2[CH2:23][C@@H:22]([OH:24])[C@H:21]([OH:25])[CH2:20]2)[CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O1CCCC1>[CH2:5]([C:12]1[C:17]([Br:18])=[CH:16][N:15]=[C:14]([N:19]2[CH2:20][C@@H:21]([O:25][CH3:3])[C@H:22]([OH:24])[CH2:23]2)[CH:13]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 697586594-Benzyl-5-bromo-2-[(3r,4r)-3,4-dihydroxypyrrolidine-1-yl]pyridine

Product 1

HCID 697590874-Benzyl-5-bromo-2-[(3r,4r)-3-hydroxy-4-methoxypyrrolidine-1-yl]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

190 mg of 60% oily sodium hydride and 0.3 ml of methyl iodide were added to a solution of 1.67 g of 4-benzyl-5-bromo-2-[(3R,4R)-3,4-dihydroxypyrrolidine-1-yl]pyridine in tetrahydrofuran, followed by stirring for 6 hours. Then, the reaction solution was extracted with ethyl acetate-water, and the organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was subjected to silica gel column chromatography and eluted with 50% ethyl acetate, to give 560 mg of the target compound.

Workup

  1. extractionThen, the reaction solution was extracted with ethyl acetate-water
  2. washthe organic phase was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. washeluted with 50% ethyl acetate

Sources & evidence

ORD record
ord-c3f07b372a154159b0c7976e47e36e49
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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