Acetaldehyde → HCID 67979996, Verbindung

HRID 1622310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1622310
C(O[C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15]([N:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:27]([O:29][CH3:30])=[O:28])[CH:23]=3)[CH2:18]2)=[O:16])([CH3:14])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.[CH:32](=O)C.[O-]S([O-])(=O)=O.[Mg+2].C([BH3-])#N.[Na+]>CO>[CH2:6]([N:8]1[CH2:9][CH2:10][C:11]([C:15]([N:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:27]([O:29][CH3:30])=[O:28])[CH:23]=3)[CH2:18]2)=[O:16])([CH3:14])[CH2:12][CH2:13]1)[CH3:32]

Komponenten

7

Edukt 5

HCID 177AcetaldehydeHCID 313Hydrochloric AcidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5003444Sodium cyanoborohydrideHCID 67979956HCID 67979956, Verbindung

Produkt 1

HCID 67979996HCID 67979996, VerbindungAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of methyl 2-{[1-(tert-butoxycarbonyl)-4-methylpiperidin-4-yl]carbonyl}-1,2,3,4-tetrahydroisoquinoline-6-carboxylate.[HCl] (0.260 g, 0.737 mmol) in MeOH (8.0 mL) was treated with acetaldehyde (0.414 g, 7.37 mmol) and MgSO4 (excess). The reaction mixture was stirred at rt for 1 h, and sodium cyanoborohydride (93 mg, 1.47 mmol) was added in portions. The resulting mixture was stirred for 3 h at rt and then filtered to remove the MgSO4. The filtrate was washed with water and brine, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by column chromatography (SiO2, 0-20% MeOH in DCM) to give methyl 2-[(1-ethyl-4-methylpiperidin-4-yl)carbonyl]-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (55 mg, 22%). LC-MS: (FA) ES+ 345; 1H NMR (400 MHz, CDCl3) δ 7.86-7.80 (m, 2H), 7.18 (d, J=7.9 Hz, 1H), 4.78 (s, 2H), 3.89 (s, 3H), 3.88-3.83 (m, 2H), 2.91 (t, J=5.5 Hz, 2H), 2.77-2.67 (m, 2H), 2.42 (q, J=7.2 Hz, 2H), 2.36-2.20 (m, 4H), 1.75-1.65 (m, 2H), 1.30 (s, 3H), 1.09 (t, J=7.2 Hz, 3H).

Aufarbeitung

  1. stirringThe resulting mixture was stirred for 3 h at rt
  2. filtrationfiltered
  3. customto remove the MgSO4
  4. washThe filtrate was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by column chromatography (SiO2, 0-20% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-47120239d9794948996d6b5b888f269a
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778931B2

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