Ethylene Glycol → 2-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl]-1,3-dioxolane

HRID 35875Notes

Reaction equation

HRID 35875 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:16]([N:23]([CH3:37])[C:24]([CH2:26][CH2:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][C@H:31]1[CH:35]=O)=[O:29])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1>[CH2:16]([N:23]([CH3:37])[C:24]([CH2:26][CH2:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][C@H:31]1[CH:35]1[O:4][CH2:1][CH2:2][O:3]1)=[O:29])=[O:25])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 14674666(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-al

Product 1

HCID 156609462-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl]-1,3-dioxolane

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Ethylene glycol (0.3 ml), p-toluenesulphonic acid (1 mg) were added to a solution of (2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-al (164 mg) in benzene (3 ml). The mixture was refluxed for 1 hr. The reaction solution was poured into a saturated aq. solution of sodium bicarbonate. The mixture was extracted with benzene. The extract was washed, dried, and evaporated. The residue was purified by column chromatography on silica gel (CH3OH-EtOAc-CH2Cl2) to give the title compound (79 mg) having the following physical data:

Workup

  1. temperatureThe mixture was refluxed for 1 hr
  2. extractionThe mixture was extracted with benzene
  3. washThe extract was washed
  4. customdried
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (CH3OH-EtOAc-CH2Cl2)

Sources & evidence

ORD record
ord-ba5f4810e8794e76af4e69fe961d5fd3
Source dataset
uspto-grants-1995_05
Patent number
US05411974

Reaction notes

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