Reaktion #2156

Reaktionsgleichung

Allyl magnesium chloride

(3S)-4-Benzyl-3-(4-fluorophenyl)-2-morpholinone

→

(2R,3S)-4-Benzyl-3-(4-fluorophenyl)-2-hydroxy-2-(prop-2-enyl)morpholine

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to below -70° C. under an inert atmosphere
2. 2
   workup.ADDITION52.4 mmol) was added dropwise over 15 minutes
3. 3
   Temperaturmaintaining the temperature below -70° C
4. 4
   Sonstigethe reaction was quenched by the addition of a saturated solution of ammonium chloride
5. 5
   ExtraktionThe resulting suspension was extracted with ethyl acetate (3×100 ml)
6. 6
   Trocknenthe combined organic extracts dried (MgSO4)
7. 7
   Einengenconcentrated in vacuo
8. 8
   Sonstigeto yield the tide compound
9. 9
   Sonstigewas used without further purification

Vorschrift

(3S)-4-Benzyl-3-(4-fluorophenyl)-2-morpholinone (13.6 g, 47.6 mmol) was dissolved in anhydrous tetrahydrofuran (200 ml) and cooled to below -70° C. under an inert atmosphere. Allyl magnesium chloride (26.2 ml of a 2.0M solution in tetrahydrofuran; 52.4 mmol) was added dropwise over 15 minutes, maintaining the temperature below -70° C. After 30 minutes, the reaction was quenched by the addition of a saturated solution of ammonium chloride and allowed to warm to room temperature. The resulting suspension was extracted with ethyl acetate (3×100 ml), and the combined organic extracts dried (MgSO4) and concentrated in vacuo to yield the tide compound in ~3:1 mixture of the lactols as a light yellow oil (15.3 g, 98%), which was used without further purification. MS (ES+) m/z 328 (M+1, 22%), 310 (M--OH, 61), 269 (100).

Quelle