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Veratraldehyde → HCID 69662836, Verbindung

HRID 1793239
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1793239
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.S(O)(O)(=O)=O.[CH3:18][C@H:19]([NH2:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][NH:27][C@@H:19]([CH3:18])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8419VeratraldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 10220277d-Amphetamine Sulfate

Produkt 1

HCID 69662836HCID 69662836, VerbindungAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11
1,2-Dichloroethane
Lösungsmittel

Versuchsvorschrift

A solution of 3,4-dimethoxybenzaldehyde (1.06 g, 6.4 mmol), (S)-1-methyl-2-phenylethylamine sulfate (1.18 g, 6.4 mmol) and triethylamine (0.89 ml, 6.4 mmol) in 1,2-dichloroethane (50 ml) was stirred at room temperature under argon for 15 min. Sodium triacetoxyborohydride (2.97 g, 14 mmol) was added over 5 min. then stirring was continued for a further 16 h. The reaction mixture was diluted with MDC (50 ml) then washed with saturated aqueous K2CO3. The aqueous phase was extracted with MDC and the combined organics washed with brine. The organic phase was dried (MgSO4) and the solvent removed in vacuo. The residue was chromatographed (silica gel, 0–100% EtOAc-pentane) to afford the title compound as a colourless oil (1.20 g, 67%).

Aufarbeitung

  1. additionThe reaction mixture was diluted with MDC (50 ml)
  2. washthen washed with saturated aqueous K2CO3
  3. extractionThe aqueous phase was extracted with MDC
  4. washthe combined organics washed with brine
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customThe residue was chromatographed (silica gel, 0–100% EtOAc-pentane)

Quellen und Nachweise

ORD-Eintrag
ord-271befcf31bf4de5be010ffc3ee4aa19
Quelldatensatz
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07078565B2

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