ChemicalBook CAS DataBase List 4,4-DIFLUORO-N-((1S)-3-OXO-1-PHENYLPROPYL)CYCLOHEXANE-1-CARBOXAMIDE

4,4-DIFLUORO-N-((1S)-3-OXO-1-PHENYLPROPYL)CYCLOHEXANE-1-CARBOXAMIDE synthesis

4synthesis methods

Product Name:4,4-DIFLUORO-N-((1S)-3-OXO-1-PHENYLPROPYL)CYCLOHEXANE-1-CARBOXAMIDE
CAS Number:376348-78-6
Molecular formula:C16H19F2NO2
Molecular Weight:295.32

376348-77-5 Synthesis

4,4-DIFLUORO-N-((1S)-3-HYDROXY-1-PHENYLPROPYL)CYCLOHEXANE-1-CARBOXAMIDE

376348-77-5
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4,4-DIFLUORO-N-((1S)-3-OXO-1-PHENYLPROPYL)CYCLOHEXANE-1-CARBOXAMIDE

376348-78-6
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Yield:376348-78-6 91%

Reaction Conditions:

with sodium hypochlorite;2,2,6,6-Tetramethyl-1-piperidinyloxy free radical;sodium hydrogencarbonate;sodium bromide in water;ethyl acetate at 0; for 0.5 h;Cooling with ice;

Steps:

5

(S)-4,4-difluoro-N-(3-hydroxy-1-phenylpropyl)cyclohexanecarboxamide (5 g), ethyl acetate (EA; 70 g), NaBr (1.7 g), NaHCO₃(1.9 g), H₂O (70 g), and (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (0.03 g) were mixed and cooled down with an ice bath before adding NaOCl (11 g). The mixture was then subjected to reaction for 30 min at 0° C. The organic phase was collected by phase separation and concentrated under reduced pressure. Crystallization with toluene gave compound (I) with 91% yield (4 g).

References:

US2019/248782,2019,A1 Location in patent:Paragraph 0026; 0029