Isopropanol → (2R)-(4E)-N-Methyl-5-(3-pyridyl)-4-penten-2-amine Hemigalactarate

HRID 489746

Reaktionsgleichung

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

Komponenten

Reaktionsbedingungen

Temperatur: 4 °C

Versuchsvorschrift

Galactaric acid (328.0 mg, 1.56 mmol) and (2R)-(4E)-N-methyl-5-(3-pyridyl)-4-penten-2-amine (600.0 mg, 3.40 mmol) were dissolved in 2-propanol (5 mL) and water (0.2 mL), assisted by heating and sonication. The hot solution was filtered to remove some insoluble material. The solvent was removed on a rotary evaporator, and the residue was dried under high vacuum, producing a cream-colored syrup. The syrup was dissolved in dry 2-propanol (5 mL) and cooled at 4° C. The resulting precipitate was filtered and dried under high vacuum to yield 700 mg (79.7%) of an off-white, crystalline powder, mp 131-134° C.

Aufarbeitung

temperatureby heating
customsonication
filtrationThe hot solution was filtered
customto remove some insoluble material
customThe solvent was removed on a rotary evaporator
customthe residue was dried under high vacuum
customproducing a cream-colored syrup
filtrationThe resulting precipitate was filtered
customdried under high vacuum
customto yield 700 mg (79.7%) of an off-white, crystalline powder, mp 131-134° C.

Quellen und Nachweise

ORD-Eintrag: ord-38ff5e1dc11f41349220c495bca034d8
Quelldatensatz: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06979695B2

Verknüpfte Notizen

Wird geladen…