Reaktion #60518

Reaktionsgleichung

(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

Ausbeute 93.2%

Lösungsmittel

ethyl acetate

tetrahydrofuran

Ethyl acetate

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle