Reaktion #1183464

Reaktionsgleichung

(S)-1-{3-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-6-aza-spiro[2.5]oct-6-yl]-propyl}-4-(3-chloro-4-trifluoromethyl-phenyl)-3-methyl-piperazin-2-one

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title compound

Ausbeute 57.3%

(S)-4-(3-Chloro-4-trifluoromethyl-phenyl)-1-[3-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-propyl]-3-methyl-piperazin-2-one

Ausbeute 57.3%

Lösungsmittel

CH3CN

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepartitioned between EtOAc and sat. aq. NaHCO3 solution
2. 2
   WaschenThe organic layer was washed with brine
3. 3
   Trocknendried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated

Vorschrift

A solution of (S)-1-{3-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-6-aza-spiro[2.5]oct-6-yl]-propyl}-4-(3-chloro-4-trifluoromethyl-phenyl)-3-methyl-piperazin-2-one (65 mg, 0.11 mmol) and hydrogen fluoride pyridine complex (70% HF; 0.26 mL) in CH3CN (3 mL) was heated at 50° C. for 16 h, then partitioned between EtOAc and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (IST Isolute® Flash NH2; EtOAc-MeOH gradient) afforded the title compound (29 mg, 56%) in a diastereomeric ratio of 97:3. Colourless gum, MS: 460.3 (M+H)+.

Quelle