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Polymorph of (S)-methyl 1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

IP.com Disclosure Number: IPCOM000185649D
Publication Date: 2009-Jul-30
Document File: 3 page(s) / 85K

Publishing Venue

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Polymorph of (S)-methyl 1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

5 g of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline is dissolved in 25 mL of dichloromethane and cooled to 0°C. During addition of 1.9 mL of methyl chloroformiate was at 0°C the pH of the reaction mixture is measured to control the pH value of the reaction mixture in the range from pH 8 to 9. After the addition of first 1.9 mL of methyl chloroformiate, another 1.9 mL of methyl chloroformiate is dissolved in 10 mL dichloromethane, and the solution of 3.5 g of potassium carbonate in 25 mL of water is added to the reaction mixture. The reaction mixture is left stirring for 15 minutes, after which the reaction mixture is slowly warmed to room temperature. After stirring for 40 minutes at room temperature, the two phases of the reaction mixture were separated and the organic phase is washed with demineralized water and anhydrous sodium sulfate (VI). The volatile components were evaporated in vacuo. The purity of the isolated product obtained was 99.4% (HPLC).

HPLC column:  Ascentis Express C8, 100 x 4,6 mm, 2.7 micrometers

Mobile phase:

A.)  0.02 ; sodium dihydrogen phosphate pH = 2.5

B.)  Acetonitrile

C.)  MeOH

Sample info:

X-ray powder diffraction patterns were obtained by Phillips PW3040/60 X’Pert PRO diffractometer; CuKa radiation 1,541874 Ǻ.

The polymorph of (S)-met...