2,2-Dimethoxypropane → 2-Benzyl-6-[cis-3,4-(dimethylmethylenedioxy)pyrrolidine-1-yl]pyridine

HRID 1359368Notes

Reaction equation

HRID 1359368 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:18][C@H:17]([OH:19])[C@H:16]([OH:20])[CH2:15]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][C:22]1(C)[C@]2(CS(O)(=O)=O)C(C[C@H:23]1CC2)=O.COC(OC)(C)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:15][C@H:16]3[O:20][C:22]([CH3:23])([CH3:21])[O:19][C@H:17]3[CH2:18]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 64952,2-DimethoxypropaneHCID 65617D-Camphorsulfonic AcidHCID 516892Sodium BicarbonateHCID 697587312-Benzyl-6-(cis-3,4-dihydroxypyrrolidine-1-yl)pyridine

Product 1

HCID 697599182-Benzyl-6-[cis-3,4-(dimethylmethylenedioxy)pyrrolidine-1-yl]pyridineYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.5 g of 2-benzyl-6-(cis-3,4-dihydroxypyrrolidine-1-yl)pyridine, 2.3 g of dl-10-camphorsulfonic acid, 20 ml of 2,2-dimethoxypropane and 5.0 ml of N,N-dimethylformamide was stirred at room temperature overnight. Aqueous saturated sodium bicarbonate was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic phase was washed with water and brine, and the solvent was removed. Then, the residue was subjected to filtration through silica gel and eluted with ethyl acetate, to give 2.87 g of the target compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic phase was washed with water and brine
  3. customthe solvent was removed
  4. filtrationThen, the residue was subjected to filtration through silica gel
  5. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-141347c0d4224e4d8930515a0805b62e
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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