Reaktion #307704

Reaktionsgleichung

3′-(4-methanesulfonylphenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl

sodium hydroxide

sodium triacetoxyborohydride

sodium hydrogen carbonate

1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde

→

title compound

Ausbeute 91.5%

3′-(4-Methanesulfonylphenyl)-4-(1,3,5-trimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazine

Ausbeute 91.5%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigereaction
2. 2
   Extraktionextract with DCM (3×20 mL)
3. 3
   Einengenconcentrate
4. 4
   Sonstigepurify
5. 5
   Waschen(silica gel chromatography, eluting with 0:100 to 12:88 methanol:DCM)

Vorschrift

Suspend 3′-(4-methanesulfonylphenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (0.191 g, 0.60 mmol) in tetrahydrofuran (4 mL). Add 1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde (0.087 g, 0.63 mmol) in tetrahydrofuran (435 μL), then sodium triacetoxyborohydride (0.13 g, 0.63 mmol). Subject reaction to ultrasound for 30 sec. then stir under nitrogen at room temperature for 7 hr. Add saturated aqueous sodium hydrogen carbonate (10 mL) followed by 2 N sodium hydroxide (1 mL) to the mixture and extract with DCM (3×20 mL). Pass the combined DCM extracts through an IST Phase Separator Frit®, concentrate and purify (silica gel chromatography, eluting with 0:100 to 12:88 methanol:DCM), to give the title compound (241.9 mg, 91%). MS (ES): m/z=441.2 [M+H]+.

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