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

HRID 2216344Notes

Reaction equation

HRID 2216344 reaction equation
[CH2:1]([C:8]1[C:13]([I:14])=[CH:12][CH:11]=[C:10]([N:15]2[CH2:19][C@H:18]([O:20]C)[C@H:17]([O:22][C:23](=O)C)[CH2:16]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.C[O-].[Na+]>O>[CH2:1]([C:8]1[C:13]([I:14])=[CH:12][CH:11]=[C:10]([N:15]2[CH2:16][C@H:17]([O:22][CH3:23])[C@H:18]([OH:20])[CH2:19]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887Methanol2×HCID 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 962WaterSolvent

Procedure

To a mixture of 7.5 g of 2-benzyl-3-iodo-6-[(3R,4S)-3-acetoxy-4-methoxypyrrolidin-1-yl]pyridine and 30 ml of methanol was added 0.33 ml of 28% methanol solution of sodium methoxide and the resultant mixture was stirred under nitrogen atmosphere at room temperature for 30 minutes. Water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (20–50% ethyl acetate/hexane), to give 6.7 g of the title compound.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (20–50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-833eeefca4a64e03b5c1ee9391ba385e
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Reaction notes

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