Reaktion #48648

Reaktionsgleichung

1-phenyl-2-nitroethane

2-(S)-(2-cyclohexylethyl)-5-(R)-formylmorpholine-4-carboxylic acid tert-butyl ester

tetrabutylammonium fluoride

→

desired compound

Ausbeute 63.8%

2(S)-(2-Cyclohexylethyl)-5-(R)-(1-(R)-hydroxy-2-(S)-nitro-3-phenylpropyl)-morpholine-4-carboxylic acid tert-butyl ester

Ausbeute 63.8%

Lösungsmittel

tetrahydrofuran

ethyl acetate

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solution overnight
2. 2
   Waschenwash with cold saturated aqueous sodium chloride (50 mL)
3. 3
   Trocknendry (sodium sulfate)
4. 4
   Filtrationfilter
5. 5
   Einengenconcentrate
6. 6
   Sonstigepurify
7. 7
   Waschen(silica gel chromatography, eluting with 2.5:97.5 ethyl acetate:dichloromethane)

Vorschrift

Add 1-phenyl-2-nitroethane (91 mg, 0.61 mmol) to a solution of 2-(S)-(2-cyclohexylethyl)-5-(R)-formylmorpholine-4-carboxylic acid tert-butyl ester (164 mg, 0.50 mmol) in dry tetrahydrofuran (6 mL). Cool to 0° C. and add tetrabutylammonium fluoride (0.25 mL of a 1 M solution in tetrahydrofuran, 0.25 mmol) and refrigerate the solution overnight. Dilute with ethyl acetate, wash with cold saturated aqueous sodium chloride (50 mL), dry (sodium sulfate), filter, concentrate and purify (silica gel chromatography, eluting with 2.5:97.5 ethyl acetate:dichloromethane) to give the desired compound as a white foam (152 mg, 63%).

Quelle