Reaktion #160191

Reaktionsgleichung

10-phenyl-8-(2,2,2-trifluoroethyl)-11-oxa-3,8-diazaspiro[5.5]undecane

4-isopropoxy-3-methyl-benzoic acid

O—(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate

diisopropylethylamine

→

desired compound

Ausbeute 76.8%

(4-isopropoxy-3-methyl-phenyl)-[10-phenyl-8-(2,2,2-trifluoroethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]methanone

Ausbeute 76.8%

Lösungsmittel

DMF

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with 1M NaOH
2. 2
   SonstigeThe organic layer was separated
3. 3
   Trocknendried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

To 10-phenyl-8-(2,2,2-trifluoroethyl)-11-oxa-3,8-diazaspiro[5.5]undecane (hydrochloride salt) (150 mg, 0.39 mmol) and 4-isopropoxy-3-methyl-benzoic acid (75 mg, 0.39 mmol) in DMF (1 mL) was added at room temperature O—(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (162 mg, 0.43 mmol) and diisopropylethylamine (337 μL, 1.94 mmol) and reaction mixture was stirred at room temperature for 30 minutes. The reaction was diluted with ethyl acetate and washed with 1M NaOH and then brine solution. The organic layer was separated, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography using 10-60% EtOAc/hexane to give the desired compound as a white foam (147 mg, 73%) ESI-MS m/z calc. 490.2. Found 491.4 (M+1)+; Retention time: 2.42 minutes (3 min run).

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