Reaktion #85713

Reaktionsgleichung

MeMgBr

(S)-tert-butyl(1-(4-acetyl-2-fluorophenyl)ethyl)carbamate

→

(S)-tert-butyl(1-(2-fluoro-4-(2-hydroxypropan-2-yl)phenyl)ethyl)carbamate

Ausbeute 92.4%

Lösungsmittel

diethyl ether

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeReaction mixture
2. 2
   Temperaturto warm to room temperature
3. 3
   workup.STIRRINGstirred for 30 min at room temperature
4. 4
   SonstigeReaction mixture
5. 5
   Temperaturwas cooled to 0° C.
6. 6
   Sonstigethen quenched with the slow addition of a saturated solution of NH4Cl
7. 7
   workup.ADDITIONdiluted with DCM
8. 8
   SonstigePhases partitioned
9. 9
   Extraktionaqueous phase extracted with DCM
10. 10
    Waschenthe organic layers combined washed with water, brine
11. 11
    Trocknendried (Na2SO4)
12. 12
    Filtrationfiltered

Vorschrift

To a solution of (S)-tert-butyl(1-(4-acetyl-2-fluorophenyl)ethyl)carbamate (296 mg, 1.05 mmol) in DCM (5.2 mL), cooled to 0° C. (water/ice bath) under N2, was added 3M MeMgBr (1.4 mL, 4.21 mmol) in diethyl ether. Reaction mixture allowed to stir for 5 min at 0° C. Then gradually allowed to warm to room temperature and stirred for 30 min at room temperature. Reaction mixture was cooled to 0° C. then quenched with the slow addition of a saturated solution of NH4Cl and diluted with DCM. Phases partitioned, aqueous phase extracted with DCM and the organic layers combined washed with water, brine, dried (Na2SO4), filtered and concentrated to (S)-tert-butyl(1-(2-fluoro-4-(2-hydroxypropan-2-yl)phenyl)ethyl)carbamate (288 mg, 0.97 mmol, 92% yield) afford as a colorless oil which slowly crystallizes upon standing. 1H NMR (400 MHz, CDCl3) δ 1.39-1.48 (m, 12H) 1.57 (s, 6H) 7.15-7.25 (m, 2H) 7.31-7.36 (m, 1H).

Quelle