Ammonium Hydroxide → HCID 21254073, compound

Participants

Reaction Steps

A mixture of 37.0 mg (0.095 mmol) of (±)-3-[3-(2-aminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-1-ethyl-3-methylpyrrolidin-2-one (from Step 5), 25.3 mg (0.105 mmol) of 4-[4-(methanesulfonamido)phenyl]butyraldehyde (EXAMPLE 4), and 57.0 mg (0.475 mmol) of anhydrous magnesium sulfate was purged with nitrogen and cooled in an ice-methanol bath at about −10° to −5° C. as 0.300 mL of dry CDCl3 was added gradually by syringe. The mixture was stirred under nitrogen at this temperature for 15-20 minutes. The septum was removed just long enough to add 4.5 mg (0.12 mmol) of sodium borohydride, and the solution was repurged with nitrogen. The mixture was stirred at −10° to −5° C. as 0.200 mL of dry methanol was added gradually, and stirring was continued at this temperature. After 25 minutes, the mixture was partitioned between 5 mL of ethyl acetate and 5 mL of water. The ethyl acetate layer was washed with brine, then dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by preparative TLC on Analtech tapered silica gel GF plates (developed in 92.5:7.5:0.75 CH2Cl2-MeOH-concd. NH4OH). Isolation of the product band (by extraction with the same solvent) gave 32.3 mg (55%) of a pale yellow, stiff foam; homogeneous by TLC in 92.5:7.5:0.75 CH2Cl2-MeOH-concd. NH4OH. 500 MHz 1H NMR (CDCl3) was consistent with the assigned structure. Mass spectrum (ESI): m/e=615.4 (M+H).

Provenance & Evidence