Acetic Acid → DehydroIvabradine-d3

HRID 420868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 420868
[CH3:1][O:2][C:3]1[C:19]([O:20][CH3:21])=[CH:18][C:6]2[CH2:7][C:8](=[O:17])[N:9]([CH2:12][CH2:13][CH2:14][NH:15][CH3:16])[CH:10]=[CH:11][C:5]=2[CH:4]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]2[C:29](=[CH:30][C:31]=1[O:32][CH3:33])[CH:28]([CH:34]=O)[CH2:27]2.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.ClCCl>[CH3:22][O:23][C:24]1[CH:25]=[C:26]2[C:29](=[CH:30][C:31]=1[O:32][CH3:33])[CH:28]([CH2:34][N:15]([CH3:16])[CH2:14][CH2:13][CH2:12][N:9]1[C:8](=[O:17])[CH2:7][C:6]3[CH:18]=[C:19]([O:20][CH3:21])[C:3]([O:2][CH3:1])=[CH:4][C:5]=3[CH:11]=[CH:10]1)[CH2:27]2

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 593787273,4-Dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbaldehydeHCID 666577367,8-Dimethoxy-3-[3-(methylamino)propyl]-1,3-dihydro-2H-3-benzazepin-2-one

Produkt 1

HCID 46240593DehydroIvabradine-d3Ausbeute 96,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Dissolve 1.1 g (3.78 mmol) of 7,8-dimethoxy-3-[3-(methylamino)propyl]-1,3-dihydro-2H-3-benzazepin-2-one in 50 ml of THF and 7 ml of dichloromethane. Add 0.69 g (4.53 mmol, 1.2 equivalent) of 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbaldehyde and 0.22 ml of acetic acid. Cool the reaction mixture to 0° C. and add 1.2 g (5.67 mmol, 1.5 equivalent) of sodium triacetoxyborohydride. The reaction is instantaneous. Evaporate to dryness. The residue is taken up in water, and the aqueous phase is adjusted to pH=8 by adding 20% sodium hydroxide solution and extracted with dichloromethane. The organic phase is washed with water, dried over MgSO4, filtered and evaporated to dryness. 1.7 g of an oil is obtained, which is purified by flash chromatography on 100 g of silica (eluant=dichloromethane/ethanol/NH4OH:95/5/0.5) to yield 1.4 g of title product in the form of a colourless oil.

Aufarbeitung

  1. customEvaporate to dryness
  2. additionby adding 20% sodium hydroxide solution
  3. extractionextracted with dichloromethane
  4. washThe organic phase is washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-f17ee31de77848b9ba885637bed0351b
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08097720B2

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