Trifluoroacetic acid → HCID 23000255, compound

Participants

Reaction Steps

To a solution of 3-chloro-5-(t-butoxycarbonylaminomethyl)-indole (2.62 g, 9.33 mmol) in CH2Cl2 (25 mL), cooled to 0° C. was added trifluoroacetic acid (10 mL). After 1 h the reaction was basified with aqueous NaOH (1 N) to pH=10, extracted with CH2Cl2 (3×) and then with CH2Cl2:MeOH (3:1). The combined organics were dried over MgSO4, filtered, and concentrated in vacuo. Purification of the resulting orange residue by flash chromatography (30×150 mm column; gradient elution with MeOH:CH2Cl2:CH2Cl2 saturated with NH3, 4:66:30 to 10:60:30 500 mL each) afforded the title compound as a yellow oil:

Provenance & Evidence