Reaktion #1135526

Reaktionsgleichung

(1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-en-1-amine

dicyclopropyl ketone

acetic acid

sodium cyanoborohydride

Acetic acid

sodium cyanoborohydride

→

title compound

(1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)-N-(dicyclopropylmethyl)but-3-en-1-amine

Lösungsmittel

methanol

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheating
2. 2
   workup.WAITwas continued overnight
3. 3
   Waschenthe organic layer was washed consecutively with K2CO3 solution and sat. NaCl solution
4. 4
   Trocknendried over K2CO3
5. 5
   Filtrationfiltered
6. 6
   Einengenthe filtrate was concentrated under reduced pressure at 60° C
7. 7
   SonstigeThe mixture was purified by flash chromatography on silica gel (eluent: DCM/MeOH, 95/5)

Vorschrift

To a solution of 2.0 g (6.84 mmol) of (1S,2R)-2-(3-chlorophenyl)-1-(4-chlorophenyl)but-3-en-1-amine (Example 115, Step E), dicyclopropyl ketone (7.54 mL, 68.4 mmol), and acetic acid (1.96 mL, 34.2 mmol) in methanol (25.0 mL) was added sodium cyanoborohydride (1.44 mL, 27.4 mmol) at rt. The resulting mixture was stirred at 50° C. for 2 days. Acetic acid (1.5 ml) and sodium cyanoborohydride (0.6 g) were added again and heating was continued overnight. 200 ml of ethyl acetate was added, and the organic layer was washed consecutively with K2CO3 solution and sat. NaCl solution, dried over K2CO3, filtered and the filtrate was concentrated under reduced pressure at 60° C. The mixture was purified by flash chromatography on silica gel (eluent: DCM/MeOH, 95/5) to give the title compound.

Quelle