Acetic Acid → HCID 10223040, compound

Participants

Reaction Steps

To a mixture of 2-methyl-5-(2-methylamino-ethyl)-1H-indole-3-carboxylic acid benzyl ester (403 mg, 1.25 mmol) and tetrahydro-4H-pyran-4-one (0.115 ML, 1.25 mmol) in dichloroethane (10 mL) was added sodium triacetoxyboro hydride (371 mg, 1.75 mmol) followed by acetic acid (0.071 mL, 1.25 mmol). The mixture was stirred at room temperature under nitrogen atmosphere for 3 hours and then partitioned between ethyl acetate 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% methanol in methylene chloride) to give 270 mg (53%) of the desired product as a white foam: mp 109-11 1° C.; MS(APCI+): m/z 407.2 (MH+); Anal. Calcd for C25H30N2O3.0.25H2O: C, 73.05; H, 7.48; N, 6.82. Found: C, 72.86; H, 7.59; N, 6.78.

Provenance & Evidence