tert-butyl N-[2-[5-(hydroxymethyl)-1H-indol-3-yl]ethyl]carbamate

Conditions: temp:-50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a cooled (-50° C.) and stirred solution of the product from Step 3 (17.4 g, 52.4 mmol) in anhydrous tetrahydrofuran (650 ml) was added dropwise via cannula diisobutylaluminium hydride (1M in toluene; 168 ml) over 23 minutes, under a nitrogen atmosphere. After being stirred at -25° C. for 1 hour, additional diisobutylaluminium hydride (1M in toluene; 40 ml) was added dropwise over 15 minutes and stirring was continued at -25° C. for further 30 minutes. Methanol (65 ml) was added dropwise (CAUTION! H2 evolution) at -35° C. followed by aqueous citric acid (10%; 450 ml) and the organic phase was decanted off. The aqueous solution was extracted with ethyl acetate (500 ml) and the combined organic phases were washed with brine (1×200 ml), dried (Na2SO4) and concentrated. Flash chromatography (silica gel, dichloromethane-methanol, 97:3) of the remaining residue gave 13.8 g (90.8%) of the title compound as a white solid. A sample recrystallised from dichloromethane showed: mp 129°-130° C.; δH (360 MHz, DMSO-d6) 10.70 (1H, br s, indole N--H), 7.44 (1H, s, Ar--H), 7.26 (1H, d, J=8.3 Hz, Ar--H), 7.10 (1H, s, Ar--H), 7.03 (1H, d, J=8.3 Hz, Ar--H), 6.86 (1H, br t, --NH--), 4.95 (1H, t, J=5.6 Hz, --OH), 4.54 (2H, d, J=5.6 Hz, --CH2OH), 3.18 (2H, m, --CH2N--), 2.78 (2H, t, J=7.2 Hz, --CH2 --), 1.38 (9H, s, t-Bu); m/z (EI) 290 (M+). (Found: C, 65.95; H, 7.82; N, 9.37. C16H22N2O3 requires: C, 66.18; H, 7.64; N, 9.65%). stirring was continued at -25° C. for further 30 minutes the organic phase was decanted off The aqueous solution was extracted with ethyl acetate (500 ml) the combined organic phases were washed with brine (1×200 ml) dried (Na2SO4) concentrated