Acetic Acid → 4-Benzyloxy-1-[2-(3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-2-oxo-ethyl]-1H-pyridin-2-one

HRID 564171Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 564171
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16](=[O:28])[C:17]2[CH:27]=[CH:26][C:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25][C:19]=3[CH:18]=2)[C:11](=[O:29])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:32](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.C([O-])(O)=O.[Na+]>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]([C:17]2[CH:27]=[CH:26][C:20]3[CH2:21][CH2:22][N:23]([CH3:32])[CH2:24][CH2:25][C:19]=3[CH:18]=2)=[O:28])[C:11](=[O:29])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 580428454-Benzyloxy-1-[2-oxo-2-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-ethyl]-1H-pyridin-2-one

Produkt 1

HCID 580428694-Benzyloxy-1-[2-(3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-2-oxo-ethyl]-1H-pyridin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To 2.00 g (5.15 mmol) 4-benzyloxy-1-[2-oxo-2-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-ethyl]-1H-pyridin-2-one (preparation 22.3) in 20 mL THF is added 0.41 mL (5.51 mmol) aqueous 37% formaldehyde solution. The mixture is acidified (pH 4-5) with acetic acid and then 1.27 g (5.97 mmol) sodium triacetoxy-borohydride is added. The reaction mixture is stirred overnight at RT, diluted with aqueous saturated NaHCO3-solution until pH 7 and THF is evaporated. The residue is diluted with EtOAc, the layers are separated and the organic phase is concentrated. The residue is elutriated in tert-butylmethylether and is collected by filtration. The residue is dissolved in DMF and purified via reverse HPLC chromatography (Waters symmetry, C18; water (0.15% formic acid)/acetonitrile 95:5 to 5:95).

Aufarbeitung

  1. customis evaporated
  2. additionThe residue is diluted with EtOAc
  3. customthe layers are separated
  4. concentrationthe organic phase is concentrated
  5. filtrationis collected by filtration
  6. dissolutionThe residue is dissolved in DMF
  7. custompurified via reverse HPLC chromatography (Waters symmetry, C18; water (0.15% formic acid)/acetonitrile 95:5 to 5:95)

Quellen und Nachweise

ORD-Eintrag
ord-491382dd6f004b7cb1febf14d69925d6
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067590B2

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