Galactaric acid → HCID 131724874, compound

HRID 2212130Notes

Reaction equation

HRID 2212130 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH:6]=[CH:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.[O:14]=[C:15]([OH:27])[C@@H:16]([C@H:18]([C@H:20]([C@@H:22]([C:24]([OH:26])=[O:25])[OH:23])[OH:21])[OH:19])[OH:17]>C(O)C.O>[O:14]=[C:15]([OH:27])[C@@H:16]([C@H:18]([C@H:20]([C@@H:22]([C:24]([OH:26])=[O:25])[OH:23])[OH:21])[OH:19])[OH:17].[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 3037582Galactaric acidHCID 20781112HCID 20781112, compound

Product 1

HCID 131724874HCID 131724874, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of (2S)-3-(2-pyrrolidin-2-ylvinyl)pyridine (120 mg, 0.689 mmol) in ethanol (2 mL), galactaric acid (72.4 mg, 0.344 mmol) was added. The mixture was heated at 70° C., sonicated and then water (1–2 drops) was added; this process was repeated until most of the solid dissolved. The remaining insoluble material was removed by filtration. To the filtrate anhydrous diethyl ether was added dropwise until it became cloudy. After 16 h at 4° C. a precipitate was formed; this was filtered and vacuum dried to give 120 mg (61.9% yield) of product as a light brown solid.

Workup

  1. customsonicated
  2. dissolutiondissolved
  3. customThe remaining insoluble material was removed by filtration
  4. additionTo the filtrate anhydrous diethyl ether was added dropwise until it
  5. customAfter 16 h at 4° C. a precipitate was formed
  6. filtrationthis was filtered
  7. customvacuum dried

Sources & evidence

ORD record
ord-180c82d78a1f466b8028b81dfb2ef63a
Source dataset
uspto-grants-2006_09
Patent number
US07101896B2

Reaction notes

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