반응 #60518

반응 방정식

(R)-1-[2-(4,4-diethylcyclohexyl)-4-(3-methoxypyrrolidin-1-yl)phenyl]piperazine

butyraldehyde

sodium hydrogencarbonate

sodium triacetoxyborohydride

acetic acid

→

(R)-1-butyl-4-[2-(4,4-diethylcyclohexyl)-4-(3-methoxypyrrolidin-1-yl)phenyl]piperazine

수율 93.2%

용매

ethyl acetate

tetrahydrofuran

Ethyl acetate

반응 조건

후처리

1. 1
   세척The separated organic layer was washed with brine
2. 2
   건조dried over anhydrous sodium sulfate
3. 3
   여과The desiccant was filtered off
4. 4
   농축the filtrate was concentrated under reduced pressure
5. 5
   기타The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

실험 절차

To a mixture of the crude product of (R)-1-[2-(4,4-diethylcyclohexyl)-4-(3-methoxypyrrolidin-1-yl)phenyl]piperazine produced in Example (98b) (160 mg), butyraldehyde (0.052 mL, 0.584 mmol) and tetrahydrofuran (7 mL) were added sodium triacetoxyborohydride (164 mg, 0.774 mmol) and acetic acid (0.022 mL, 0.384 mmol) in that order, followed by stirring for 1 hour at room temperature. Ethyl acetate and saturated aqueous solution of sodium hydrogencarbonate were added to the reaction mixture and extraction was performed with ethyl acetate. The separated organic layer was washed with brine and then dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 170 mg of (R)-1-butyl-4-[2-(4,4-diethylcyclohexyl)-4-(3-methoxypyrrolidin-1-yl)phenyl]piperazine as a light brown oil.

출처