Reaktion #218369

Reaktionsgleichung

51

(R)-Phenyl{(2S)-4-[(1R)-1-phenylethyl]morpholin-2-yl}methyl methanesulphonate

potassium carbonate

2-trifluoromethylbenzenethiol

→

oil

Ausbeute 71.0%

(2S)-4-[(1R)-1-Phenylethyl]-2-((S)-phenyl{[2-(trifluoromethyl)phenyl]thio}methyl)morpholine

Ausbeute 71.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigein dry
2. 2
   Sonstigedegassed dimethylformamide (0.5 ml)
3. 3
   workup.ADDITIONThe reaction mixture was diluted with water
4. 4
   Extraktionextracted with diethyl ether
5. 5
   WaschenThe extracts was washed with water and brine
6. 6
   Trocknendried over magnesium sulphate
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated

Vorschrift

A mixture of 51 (0.035 g, 0.093 mmol), potassium carbonate (0.026 g, 0.19 mmol) and 2-trifluoromethylbenzenethiol (0.084 g, 0.47 mmol) in dry, degassed dimethylformamide (0.5 ml) was stirred under nitrogen at room temperature for 3 days. The reaction mixture was diluted with water and extracted with diethyl ether. The extracts was washed with water and brine, dried over magnesium sulphate, filtered and evaporated to give a colourless oil (0.03 g, 71%). Purification by flash column chromatography (eluent: ethyl acetate/heptane 20/80 [v/v]) gave 52 as a colourless oil (0.03 g, 71%); MW 457.56; C26H26F3NOS 1H NMR (CDCl3) 7.53 (1H, d), 7.10-7.28 (13H, m), 4.39 (1H, d), 3.85-4.04 (2H, m), 3.8 (1H, td), 3.35 (1H, q), 2.70 (1H, d), 2.40 (1H, d), 2.30 (1H, td), 2.10-2.20 (1H, m), 1.29 (3H, d). m/z [M+H]+ 458.

Quelle