Reaktion #446908

Reaktionsgleichung

dimethylamine

HCl

HCl

hydroxybenzotriazole

3-indolepyruvic acid

→

N,N-dimethyl 3-indolepyruvamide

Lösungsmittel

CH2Cl2

tetrahydrofuran

4-methylmorpholine

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONAfter dissolving
2. 2
   Sonstigeleaving the bath temperature
3. 3
   Sonstigeto rise up to room temperature
4. 4
   Waschenthe organic solution was washed in sequence with 5% NaHCO3 (10×25 ml), saturated NaCl solution (3×25 ml), 5% KHSO4 (10×25 ml) and saturated NaCl solution up to neutrality
5. 5
   workup.WAITAfter standing for one night on anhydrous Na2SO4
6. 6
   Filtrationthis was filtered off
7. 7
   Sonstigethe mixture was purified by flash chromatography (silica gel, eluent CH2Cl2 25/n-propanol 1,5)

Vorschrift

A solution of 500 mg 3-indolepyruvic acid in 25 ml anhydrous tetrahydrofuran on an ice-salt bath, under argon atmosphere and under stirring was additioned in swift succession with: 400 mg hydroxybenzotriazole (HOBt) and 570 mg 1-(3-dimethylaminopropyl)-3-ethylcarbimdie.HCl (EDC.HCl). After dissolving and still maintaining the ice-salt bath, 240 mg dimethylamine.HCl were added dissolved in 10 ml anhydrous tetrahydrofuran and 325 microliters 4-methylmorpholine (NMM). The yellowish gold solution was maintained under stirring for one night, leaving the bath temperature to rise up to room temperature. The volume was then tripled adding CH2Cl2 and the organic solution was washed in sequence with 5% NaHCO3 (10×25 ml), saturated NaCl solution (3×25 ml), 5% KHSO4 (10×25 ml) and saturated NaCl solution up to neutrality. After standing for one night on anhydrous Na2SO4, this was filtered off, the mixture was purified by flash chromatography (silica gel, eluent CH2Cl2 25/n-propanol 1,5).

Quelle