Water → Ispronicline hemigalactarate

HRID 1711524Notes

Reaction equation

HRID 1711524 reaction equation
[CH3:1][NH:2][C@H:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[CH:13]=1)[CH3:4].[O:18]=[C:19]([OH:31])[C@@H:20]([C@H:22]([C@H:24]([C@@H:26]([C:28]([OH:30])=[O:29])[OH:27])[OH:25])[OH:23])[OH:21].O>C(O)C>[O:18]=[C:19]([OH:31])[C@@H:20]([C@H:22]([C@H:24]([C@@H:26]([C:28]([OH:30])=[O:29])[OH:27])[OH:25])[OH:23])[OH:21].[CH3:1][NH:2][C@H:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[CH:13]=1)[CH3:4].[CH3:1][NH:2][C@H:3]([CH2:5]/[CH:6]=[CH:7]/[C:8]1[CH:9]=[N:10][CH:11]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[CH:13]=1)[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 3037582Galactaric acidHCID 9824145Ispronicline

Product 1

HCID 72941778Ispronicline hemigalactarateYield 26%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

(2S)-(4E)-N-Methyl-5-(5-isopropoxy-3-pyridyl)-4-penten-2-amine (2.00 g, 8.55 mmol) was dissolved in ethyl alcohol (20 mL), assisted by warming to 70° C. The warm solution was treated with galactaric acid (900 mg, 4.27 mmol) in one portion, followed by the dropwise addition of water (0.5 mL). The solution was filtered while hot to remove some insoluble material. The filtrate was allowed to cool to ambient temperature. The resulting crystals were filtered, washed with anhydrous diethyl ether, and dried under vacuum at 40° C. to yield a white, crystalline powder (750 mg, 26.0%), mp 140-143° C.

Workup

  1. filtrationThe solution was filtered while hot
  2. customto remove some insoluble material
  3. temperatureto cool to ambient temperature
  4. filtrationThe resulting crystals were filtered
  5. washwashed with anhydrous diethyl ether
  6. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-6713298624234ebba66f522109870303
Source dataset
uspto-grants-2010_09
Patent number
US07790757B2

Reaction notes

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