Reaktion #1721098

Reaktionsgleichung

4-Aminomethylbenzoic acid methyl ester, hydrochloride salt

potassium carbonate

4-Cyclopropylidenecyclohexanone

sodium triacetoxyborohydride

→

4-[(4-cyclopropylidenecyclohexylamino)methyl]benzoic acid methyl ester

Ausbeute 35.0%

Lösungsmittel

dichloromethane

dichloromethane

1,2 dichloropropane

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe next day the organic phase was isolated
2. 2
   Trocknendried (MgSO4)
3. 3
   workup.ADDITIONwas added
4. 4
   Waschenwashed with aqueous saturated sodium hydrogen carbonate (2×30 mL) and water (5×30 mL)
5. 5
   TrocknenThe organic phase was dried (MgSO4)
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe residue was purified by flash chromatography (50 g silica)

Vorschrift

4-Aminomethylbenzoic acid methyl ester, hydrochloride salt (2.2 g, 11 mmol) was suspended in 1,2 dichloropropane (30 mL) and an aqueous saturated solution of potassium carbonate (15 mL) was added. The next day the organic phase was isolated and dried (MgSO4). 4-Cyclopropylidenecyclohexanone (1.5 g, 11 mmol) dissolved in dichloromethane (15 mL) was added followed by addition of acetic acid (400 μL) and sodium triacetoxyborohydride (3.3 g, 16.5 mmol). After 72 hours at 20° C. the reaction mixture was diluted with dichloromethane (50 mL) and washed with aqueous saturated sodium hydrogen carbonate (2×30 mL) and water (5×30 mL). The organic phase was dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography (50 g silica) using ethyl acetate and methanol (97:3) as eluent to give 1.1 g of 4-[(4-cyclopropylidenecyclohexylamino)methyl]benzoic acid methyl ester.

Quelle