Reaktion #1280464

Reaktionsgleichung

(3R)-3-Amino-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester hydrochloride

2-bromomethyl-6-chlorobenzoic acid methyl ester

triethylamine

NaHCO3

→

(R)-methyl 3-(7-chloro-1-oxoisoindolin-2-yl)-2,3-dihydro-1H-indene-5-carboxylate

Lösungsmittel

toluene

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was refluxed for 16 h
2. 2
   Sonstigethe phases were separated
3. 3
   ExtraktionThe organic phase was extracted with 0.05 N HCl solution and sat. NaCl solution
4. 4
   Trocknendried over MgSO4
5. 5
   SonstigeConcentration of the organic phase yielded the crude product, which
6. 6
   Sonstigewas purified by column chromatography (ethyl acetate:cyclohexane, 3:1)

Vorschrift

(3R)-3-Amino-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester hydrochloride (A-01) (1.757 mmol, 1 eq) was added to a solution of 2-bromomethyl-6-chlorobenzoic acid methyl ester (1 eq) in toluene (5.4 ml) and triethylamine (2.1 eq). The reaction mixture was refluxed for 16 h. Then sat. NaHCO3 solution (20 ml) and ethyl acetate (50 ml) were added to the mixture and the phases were separated. The organic phase was extracted with 0.05 N HCl solution and sat. NaCl solution and dried over MgSO4. Concentration of the organic phase yielded the crude product, which was purified by column chromatography (ethyl acetate:cyclohexane, 3:1). The desired product (R)-methyl 3-(7-chloro-1-oxoisoindolin-2-yl)-2,3-dihydro-1H-indene-5-carboxylate (D-01) was thus obtained. Yield: 72%

Quelle