Sodium Bicarbonate → HCID 86649011, Verbindung

HRID 1879750Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1879750
[Cl:1][C:2]1[C:3]([CH:16]=O)=[N:4][CH:5]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[CH2:13][O:14][CH3:15])[N:7]=1.[CH2:18]([NH:25][CH2:26][C@@H:27]([OH:31])[CH2:28][O:29][CH3:30])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(#N)C.C(O)(=O)C>[CH2:18]([N:25]([CH2:16][C:3]1[C:2]([Cl:1])=[N:7][C:6]([N:8]2[CH2:12][CH2:11][CH2:10][CH:9]2[CH2:13][O:14][CH3:15])=[CH:5][N:4]=1)[CH2:26][C@@H:27]([OH:31])[CH2:28][O:29][CH3:30])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 34179216HCID 34179216, VerbindungHCID 866490103-Chloro-5-[2-(methoxymethyl)pyrrolidin-1-yl]pyrazine-2-carbaldehyde

Produkt 1

HCID 86649011HCID 86649011, VerbindungAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 3-chloro-5-[2-(methoxymethyl)pyrrolidin-1-yl]pyrazine-2-carbaldehyde (511 mg), (2R)-1-(benzylamino)-3-methoxypropan-2-ol (469 mg) and acetic acid (343 μL) in acetonitrile (10 mL) was added sodium triacetoxyborohydride (636 mg), and the mixture was stirred at room temperature for 14.5 hr. To the reaction mixture was added dropwise a saturated sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient: 10→50% ethyl acetate/hexane) to give the title compound (583 mg, 67%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent gradient: 10→50% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f1ec22ac7c3149ceac164353224cb374
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318722B2

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