Water → 2-Benzyl-3-iodo-6-[(3R,4S)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridine

HRID 1359341Notes

Reaction equation

HRID 1359341 reaction equation
C[O-].[Na+].[CH2:4]([C:11]1[C:16]([I:17])=[CH:15][CH:14]=[C:13]([N:18]2[CH2:22][C@H:21]([O:23]C)[C@H:20]([O:25][C:26](=O)C)[CH2:19]2)[N:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O>CO>[CH2:4]([C:11]1[C:16]([I:17])=[CH:15][CH:14]=[C:13]([N:18]2[CH2:19][C@H:20]([O:25][CH3:26])[C@H:21]([OH:23])[CH2:22]2)[N:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 693630452-benzyl-3-iodo-6-[(3R,4S)-3-acetoxy-4-methoxypyrrolidin-1-yl]pyridine

Product 1

HCID 693629412-Benzyl-3-iodo-6-[(3R,4S)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridineYield 98.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A 28% solution of sodium methoxide in 0.33 ml of methanol was added to a mixture of 7.5 g of 2-benzyl-3-iodo-6-[(3R,4S)-3-acetoxy-4-methoxypyrrolidine-1-yl]pyridine and 30 ml of methanol, followed by stirring at room temperature for 30 minutes in a nitrogen atmosphere. Water was added thereto, and the mixture was extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography using 20-50% ethyl acetate, to give 6.7 g of the target compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c2a3f34a295f4319b4f714effc28a578
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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