Morpholine → HCID 145847173, compound

Participants

Reaction Steps

A solution of 1-tert-Butoxycarbonyl-3-(tert-butoxycarbonylcarbamimidoyl)-5-(2-[allyloxycarbonylamino]ethyl)indole (reference example 8) (0.199 g, 0.409 mmol), 50 mg tetrakis(triphenylphosphine)palladium (0), and 0.078 mL (0.90 mmol) morpholine in 20 mL CH2Cl2 is stirred for one hour. TLC showed some starting material present, so another 50 mg palladium catalyst is added. After stirring 45 minutes, the reaction mixture is concentrated, and the residue chromatographed (10:1 CH2Cl2:7N NH3 in MeOH) to provide the product as a yelow solid. 1H NMR (CDCl3): δ 1.57 (9H, s), 1.64 (9H, s), 2.88 (4H, m), 7.23 (1H, dd, J1=8.7 Hz, J2=1.2 Hz), 7.77 (1H, s), 8.16 (1H, d, J=8.7 Hz), 8.25 (1H, s). MS (EI) m/z 402 M+.

Provenance & Evidence