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

HRID 968391

Reaction equation

[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]

Participants

Conditions

Temperature: 4 °C

Procedure

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.

Workup

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.

Sources & evidence

ORD record: ord-43c6b9f781254f71aee7a5354ee4c425
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06958399B2

Linked notes

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