Reaktion #1018935

Reaktionsgleichung

(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)ethyl pivalate

NaOH

→

desired product

Ausbeute 64.0%

(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)ethanol

Ausbeute 64.0%

Lösungsmittel

THF

methanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe resulting mixture was extracted with ethyl acetate
2. 2
   WaschenThe organic layer was washed with brine
3. 3
   Sonstigedried
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe obtained residue was purified by prep-HPLC

Vorschrift

To a stirred solution of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)ethyl pivalate (5.6 mg, 0.011 mmol) in THF and methanol (1.5 mL/0.5 mL) was added 2 M NaOH solution (0.5 mL, excess) at 0° C. The mixture was stirred at 50° C. for 3 hours, diluted with water and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated in vacuo. The obtained residue was purified by prep-HPLC to provide the desired product (3.0 mg, 64%). LCMS-ESI+ (m/z): 427.3, 429.2 (M+H)+.

Quelle