Triethylamine → 1H-Indolamine

Crude 2-methyl-2-pyrrolidin-1-yl-propan-1-ol (0.849 g, 5.94 mmol, 1 eq) was suspended in dry acetonitrile (30 mL) under Ar. Triethylamine (1.4 mL, 10 mmol, 1.7 eq) was added followed by the addition of toluenesulfonyl chloride (1.05 g, 5.50 mmol, 1.0 eq). The reaction mixture was stirred at room temperature for 1 hour. After 4 hours, the reaction was treated with 2-methyl-3-benzyloxycarbonyl-5-hydroxyindole (1.5 g; 5.5 mmol, 1 eq) and potassium carbonate (1.38 g, 10 mmol, 1.7 eq.). The reaction was heated to reflux and followed by TLC (ethyl acetate/methanol/triethylamine 87/10/3). After 23 hours, the reaction was loaded directly on silica gel and chromatographed (ethyl acetate/methanol/triethylamine 87/10/3). Impure product was further purified by reverse-phase prep-HPLC 10-100% Acetonitrile/water, 0.1% TFA. 0.040 g (5% yield) of the indole-amine was obtained as a brown semisolid: LC/MS (ESI+) 407 (M+1), Anal. (C24H30N2O2.TFA.1.0H2O) C, H, N.

1. waitAfter 4 hours
2. temperatureThe reaction was heated
3. temperatureto reflux
4. waitAfter 23 hours
5. customchromatographed (ethyl acetate/methanol/triethylamine 87/10/3)
6. customImpure product was further purified by reverse-phase prep-HPLC 10-100% Acetonitrile/water, 0.1% TFA

ORD-Eintrag

ord-e75ea8e849854a179a962faf161b13e7

Quelldatensatz

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06951848B2