Acetaldehyde → 5-Diethylaminomethyl-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

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Reaction Steps

To a mixture of 5-aminomethyl-2-methyl-1H-indole-3-carboxylic acid benzyl ester, hydrochloride (300 mg, 0.91 mmol, Example 63, Step E) and in dichloroethane (40 mL) was added acetaldehyde (0.1 mL, 1.82 mmol). The mixture was stirred for 0.5 hour and then sodium triacetoxyborohydride (289 mg, 1.37 mmol) was added. The mixture was stirred at room temperature overnight and then partitioned between methylene chloride and water. The organic phase was washed with saturated sodium bicarbonate solution and brine, dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo to give a solid residue, which was purified by chromatography (5%-15% methanol in methylene chloride) to give 107 mg (34%) of the desired product as a white solid: mp 106-108° C.; MS(APCI+): m/z 351.1 (MH+); Anal. Calcd for C22H26N2O2.0.25H2O: C, 74.44; H, 7.52; N, 7.89. Found: C, 74.30; H, 7.51; N, 7.79.

Provenance & Evidence