反应详情

Add a solution of 1,2,3,4-tetrahydroisoquinoline (Aldrich Chemical Company) in absolute ethanol (0.0465 g, 0.200 M solution, 1.745 mL, 2.0 equiv.) to a reaction tube. Add absolute ethanol (3 mL) to the reaction tube and then add a solution of (R)-1-methyl-3-(3-oxiranylmethoxy-phenyl)-1H-thieno[3,2-c]pyrazole and absolute ethanol (example 8, 0.050 g, 0.200 M solution, 0.875 mL). Shake the reaction mixture under Argon at reflux temperature overnight in a Bohdan apparatus. Cool and concentrate to remove the solvent. Purify the residue by flash chromatography (5 g silica gel SepPak cartridge) eluting in step gradient fashion sequentially with 2% and 5% methanol in dichloromethane, and dichloromethane:methanol:ammonium hydroxide solution, 90:9:1. Combine and concentrate the desired fractions to give the title compound (0.0796 g), LC/MS (APCI, condition 3) m/e 420 (MH+), retention time 5.16 min.

1. temperatureShake the reaction mixture under Argon at reflux temperature overnight in a Bohdan apparatus
2. temperatureCool
3. concentrationconcentrate
4. customto remove the solvent
5. customPurify the residue by flash chromatography (5 g silica gel SepPak cartridge)
6. washeluting in step gradient fashion sequentially with 2% and 5% methanol in dichloromethane, and dichloromethane
7. concentrationCombine and concentrate the desired fractions