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Synthesizing method of chiral amino indanone

A synthesis method and amino technology, applied in chemical instruments and methods, preparation of organic compounds, production of bulk chemicals, etc., can solve the problems of long route and harsh reaction conditions, and achieve the effect of short synthesis route and excellent synthesis method.

Inactive Publication Date: 2013-01-23
JIANGSU BAOZONG & BAODA PHARMACHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Literature method (2) route is longer, and reaction conditions are harsh

Method used

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  • Synthesizing method of chiral amino indanone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] Weigh 3g of N-phthaloyl-L-phenylalanine into a 250mL round-bottomed flask with a magnetic stirrer, add 20ml of polyphosphoric acid, put it in an oil bath, install a reflux device, and put it in an oil bath Heat up to 130°C, react for 3 hours; then cool to room temperature, add 60ml of water to the flask, add 30ml of CH 2 Cl 2 Extracted 3 times, the organic phase was extracted with anhydrous MgSO 4 Dry and filter, and the filtrate was removed from the solvent on a rotary evaporator to obtain a light yellow solid; column chromatography was performed with an eluent of petroleum ether / ethyl acetate (volume ratio 4:1) to obtain a white solid (S)-2- Phthalimido-1-indanone 2.1030g, the yield is 74.6%; [α] D 23 =-21.5 (c 0.46, chloroform); melting point is 203-205°C; IR, v (cm -1 ): 1723, 1602, 1461, 1446, 1383, 1266, 1115, 1074, 1048, 974, 872, 760, 706, 643; 1 H NMR (300MHz, CDCl 3 ), δ (ppm): 3.40 (dd, J 1 =16Hz,J 2 =6Hz, 1H), 3.60(dd, J 1 =16Hz,J 2 =8.4Hz, 1H), 5....

Embodiment 2

[0013] Similar to the operation of Example 1, N-phthaloyl-D-phenylalanine was used as the raw material to obtain 2.2101 g of (R)-2-phthalimide-1-indanone as a white solid, producing The rate is 78.4%; [α] D 23 =-20.8 (c 0.6, chloroform); melting point is 202-204°C; IR, 1 H NMR agrees.

Embodiment 3

[0015] Similar to the operation of Example 1, N-phthaloyl-DL-phenylalanine was used as the raw material to obtain 2.0800 g of (±)-2-phthalimido-1-indanone as a white solid, producing The rate is 73.8%; the melting point is 193-195°C; IR, 1 H NMR agrees.

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Abstract

The invention discloses a synthesizing method of chiral amino indanone. The chiral amino indanone as a chiral midbody is used for the synthesis of drugs, natural products and chiral ligands. The synthesizing method of the chiral amino indanone comprises the following steps of: reacting L-phenylalanine with phthalic anhydride to obtain (S)-2-phthalimide-3-phenylpropionic acid, and subjecting the (S)-2-phthalimide-3-phenylpropionic acid to an intramolecular friedel-crafts acylation reaction under the catalysis of polyphosphoric acid to obtain (S)-2-phthalimide-1-indanone; heating for hydrolyzing to strip a phthalyl protective group of the (S)-2-phthalimide-1-indanone contained in a concentrated hydrochloric acid and glacial acetic acid solution so as to obtain (S)-2-amino-1-indanone hydrochloride; substituting the L-phenylalanine by the D-phenylalanine so as to obtain (R)-2-amino-1-indanone hydrochloride, and using DL-phenylalanine so as to obtain a racemic product. The synthesizing method has the characteristics of environment friendliness, atom economy, low cost and easy obtaining of raw materials, and the like.

Description

technical field [0001] The present invention belongs to the synthesis of organic chemistry, organic synthesis and chiral compounds, and more specifically uses L configuration, D configuration or DL ​​configuration phenylalanine to synthesize (S) configuration, (R) configuration or elimination Rotation of 2-amino-1-indanone hydrochloride. Background technique [0002] (S)- or (R)-2-amino-1-indanone is a useful chiral intermediate, which can be used in the synthesis of drugs, natural products and chiral ligands, such as the synthesis of chiral 2-amino- 1-Indanol. [0003] Bibliographical reports synthesize the method for chiral 2-amino-1-indanone mainly to contain, (1) protect phenylalanine with phthaloyl or N-ethoxycarbonyl, use thionyl chloride or phosphorus trichloride Chloride into acid chloride, then use Lewis acid aluminum trichloride and ferric chloride to catalyze intramolecular Friedel-Crafts acylation, and then remove the protecting group (F.Effenberger, et al.Chem...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C225/20C07C221/00
CPCY02P20/55
Inventor 曾庆乐赵蓉
Owner JIANGSU BAOZONG & BAODA PHARMACHEM
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