3-(2-dimethylamino-ethyl)-1H-indole-5-carbaldehyde → 5-Hydroxymethyl-N,N-dimethyltryptamine

HRID 71040Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 71040
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]=[O:15])[CH:12]=2)[NH:7][CH:6]=1>CO>[CH3:16][N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:14][OH:15])[CH:12]=2)[NH:7][CH:6]=1

Komponenten

3

Edukt 1

HCID 99908943-(2-dimethylamino-ethyl)-1H-indole-5-carbaldehyde

Produkt 1

HCID 102628495-Hydroxymethyl-N,N-dimethyltryptamineAusbeute 104,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A 50 ml hydrogenation bomb is charged with 3-(2-dimethylamino-ethyl)-1H-indole-5-carbaldehyde (Example 13) (1.0 g, 4.62 mmol) and methanol (10 mL). The bomb is purged with hydrogen (three times to 200 psi and release to atmospheric pressure), and then pressurised to 200 psi. After stirring for one hour, the pressure is released, and a solution of [Rh DiPFc (COD)]BF4 (6.6 mg, S/C=500) in methanol (1 ml) is added through a septum port. The bomb is pressurized with hydrogen to 200 psi, and left stirring at ambient temperature for 18 hours. Removal of the solvent from the hydrogenation mixture gives the title product (1.05 g, quant.) as an oil.

Aufarbeitung

  1. customThe bomb is purged with hydrogen (three times to 200 psi and release to atmospheric pressure)
  2. additiona solution of [Rh DiPFc (COD)]BF4 (6.6 mg, S/C=500) in methanol (1 ml) is added through a septum port
  3. waitleft
  4. stirringstirring at ambient temperature for 18 hours
  5. customRemoval of the solvent from the hydrogenation mixture

Quellen und Nachweise

ORD-Eintrag
ord-6ab4bc50872d4219b231a2c439a54d94
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822702B2

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