N-[2-(5-amino-1H-indol-3-yl)ethyl]acetamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product from example 3 (5 mmol) is then treated with allyl chloroformate in the same manner as above, and purified on silica gel with 5% methanol in chloroform as eluent. purified on silica gel with 5% methanol in chloroform as eluent

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product from Example 3 is dissolved in acetic acid-water (1:2, 3 mL) and sodium cyanate (2 mmol) added. This is stirred until a brownish gum is precipitated. The mixture is extracted with chloroform (3×30 mL), and the organic extracts washed with saturated sodium bicarbonate, dried with magnesium sulfate and the solvent evaporated in vacuo. The resulting product is purified by reverse-phase HPLC as above. is precipitated The mixture is extracted with chloroform (3×30 mL) the organic extracts washed with saturated sodium bicarbonate dried with magnesium sulfate the solvent evaporated in vacuo The resulting product is purified by reverse-phase HPLC as above

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product from Example 2 (0.05 mmol) is taken into ethanol (3 mL) and hydrogenated 6 h at 3 atmospheres of H2 pressure over a catalytic amount of 10% Pd/C. The catalyst is removed by filtration through Celite and the solvent removed in vacuo, affording the title compound. This product is somewhat air sensitive and is used immediately for subsequent reactions. The catalyst is removed by filtration through Celite the solvent removed in vacuo