反应详情

温度

23 °C

To 400 mg (1.66 mmol) of 1-(6-methoxy-naphthalen-2-yl)-piperazine in 40 mL of CH2Cl2 and 100 mg of glacial HOAc at 23° C. was added 384 mg (1.66 mmol) of 4-(5-fluoro-1H-indol-3-yl)-cyclohex-3-enone followed by 216 mg, (1.89 mmol) of Na(OAc)3BH. After stirring at 23° C. for 12 hours, the reaction mixture was transferred to a separatory funnel and partitioned between water and CH2Cl2. The organics were washed with brine, dried over MgSO4, and chromatographed on silica gel eluting with 20:1 EtOAc:2 M NH, in MeOH. The product fractions were pooled, stripped, and treated with 115 mg (1.3 mmol) of (CO2H)2 in absolute EtOH to give 640 mg (1.40 mmol, an 84% yield) of the oxalate salt of the title compound as a white crystalline solid. mp: 200-203° C.; MS (ES) m/z 458 (M)+.

1. customthe reaction mixture was transferred to a separatory funnel
2. custompartitioned between water and CH2Cl2
3. washThe organics were washed with brine
4. dry with materialdried over MgSO4
5. customchromatographed on silica gel eluting with 20:1 EtOAc
6. customto give 640 mg (1.40 mmol