Reaktion #1604805

Reaktionsgleichung

ethyl 4-((2′-chloro-4′,4′-difluoro-4′,5′-dihydrospiro[piperidine-4,7′-thieno[2,3-c]pyran]-1-yl)methyl)-1-(3-chloro-2-pyridyl)-1H-pyrazole-3-carboxylate

lithium borohydride

→

title compound

Ausbeute 39.0%

[4-[(2-Chloro-4,4-difluoro-spiro[5H-thieno[2,3-c]pyran-7,4′-piperidine]-1′-yl)methyl]-1-(3-chloro-2-pyridyl)pyrazol-3-yl]methanol

Ausbeute 39.0%

Lösungsmittel

tetrahydrofuran

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter completion, the reaction mixture was quenched with water (10 mL)
2. 2
   Extraktionextracted with ethyl acetate (2×25 mL)
3. 3
   TrocknenThe combined organic extracts are dried over sodium sulfate
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe crude mixture is purified by column chromatography over silica gel eluting with dichloromethane/methanol (97:3)

Vorschrift

To a solution of ethyl 4-((2′-chloro-4′,4′-difluoro-4′,5′-dihydrospiro[piperidine-4,7′-thieno[2,3-c]pyran]-1-yl)methyl)-1-(3-chloro-2-pyridyl)-1H-pyrazole-3-carboxylate (0.4 g, 0.73 mmol) in tetrahydrofuran (5 mL) and ethanol (5 mL) is added lithium borohydride (1.80 mL, 2.0 M solution in tetrahydrofuran, 3.68 mmol) at 0° C. and stirred at room temperature for 16 h. After completion, the reaction mixture was quenched with water (10 mL) and extracted with ethyl acetate (2×25 mL). The combined organic extracts are dried over sodium sulfate and concentrated in vacuo. The crude mixture is purified by column chromatography over silica gel eluting with dichloromethane/methanol (97:3) to yield 0.14 g (39%) of the title compound. MS (m/z): 500 (M+1).

Quelle