ethyl 3-[2-(N-tert-butyloxycarbonylamino)ethyl]-1H-indole-5-acetate → 3-[2-(N-Tert-butyloxycarbonylamino)ethyl]-5-(2-hydroxyethyl)-1H-indole

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Reaction Steps

Diisobutylaluminium hydride reduction of ethyl 3-[2-(N-tert-butyloxycarbonylamino)ethyl]-1H-indole-5-acetate using the conditions described for Intermediate 1 (Step 4) afforded the title compound as a colourless thick oil, after purification by flash chromatography (silica gel, diethyl ether); δH (250 MHz, CDCl3) 8.03 (1H, br s, indole N--H), 7.44 (1H, s, Ar--H), 7.32 (1H, d, J=8.3 Hz, Ar--H), 7.07 (1H, dd, J=8.3 and 1.6 Hz, Ar--H), 7.02 (1H, d, J=2.2 Hz, Ar--H), 4.60 (1H, br s, --NH--), 3.89 (2H, t, J=6.5 Hz, --CH2OH), 3.45 (2H, m, --CH2N--), 2.97 (2H, t, J=6.5 Hz, --CH2CH2OH), 2.93 (2H, t, J=6.8 Hz, --CH2 -- ), 1.43 (9H, s, t--Bu); m/z (CI) 303 (M+ -1). (Found: m/z 304.1759. C17H24N2O requires: m/z 304.1787).

Provenance & Evidence