반응 #45142

반응 방정식

Sodium triacetoxyborohydride

ethyl 4-((3R,5S)-3,5-dimethylpiperazin-1-yl)benzoate

acetic acid

→

ethyl 4-((3R,5S)-3,4,5-trimethylpiperazin-1-yl)benzoate

수율 70.9%

용매

methanol

반응 조건

후처리

1. 1
   기타The reaction mixture was quenched with saturated NaHCO3 (15 mL) to pH7
2. 2
   기타the crude product was purified by ion exchange chromatography
3. 3
   세척The desired product was eluted from the column
4. 4
   기타evaporated to dryness
5. 5
   기타to afford an oil
6. 6
   기타The crude product was purified by silica column chromatography
7. 7
   세척eluting with a gradient of 0 to 5% MeOH in DCM
8. 8
   기타Pure fractions were evaporated to dryness

실험 절차

Sodium triacetoxyborohydride (5.30 g, 25.00 mmol) was added to ethyl 4-((3R,5S)-3,5-dimethylpiperazin-1-yl)benzoate (2.62 g, 10 mmol), and acetic acid (1.145 mL, 20.00 mmol) in methanol (15 mL) at 25° C. The resulting solution was stirred at ambient temperature for 18 h. The reaction mixture was quenched with saturated NaHCO3 (15 mL) to pH7 and the crude product was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 7M NH3/MeOH and evaporated to dryness to afford an oil. The crude product was purified by silica column chromatography, eluting with a gradient of 0 to 5% MeOH in DCM. Pure fractions were evaporated to dryness to afford ethyl 4-((3R,5S)-3,4,5-trimethylpiperazin-1-yl)benzoate (1.960 g, 70.9%) as a yellow oil. MS: m/z 277 (MH+).

출처