تفاعل #45142

معادلة التفاعل

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

المردود 70.9%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction mixture was quenched with saturated NaHCO3 (15 mL) to pH7
2. 2
   أخرىthe crude product was purified by ion exchange chromatography
3. 3
   غسيلThe desired product was eluted from the column
4. 4
   أخرىevaporated to dryness
5. 5
   أخرىto afford an oil
6. 6
   أخرىThe crude product was purified by silica column chromatography
7. 7
   غسيلeluting with a gradient of 0 to 5% MeOH in DCM
8. 8
   أخرىPure fractions were evaporated to dryness

الإجراء التجريبي

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+).

المصدر