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Novel use of chiral (R/S)-a-phenethylamine(+/-)-tartrate

A tartrate, a new-purpose technology, applied in the field of known compounds, can solve the problems of complicated operation and low efficiency

Inactive Publication Date: 2007-08-15
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Chiral cyanohydrins can be separated from racemates, but the operation is complicated and the efficiency is low

Method used

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  • Novel use of chiral (R/S)-a-phenethylamine(+/-)-tartrate

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Embodiment Construction

[0023] R / S-a-phenylethylamine: produced by Changzhou Kerunda Technology Co., Ltd.

[0024] (+ / -)-tartaric acid: produced by Hangzhou Linan Jinlong Chemical Co., Ltd.

[0025] (1) Preparation of chiral catalyst

[0026] 1a: Preparation of R-a-phenethylamine-(-)tartrate

[0027] Preparation of R-a-phenylethylamine-(-)tartaric acid salt

[0028] In a 250ml Erlenmeyer flask, add 6.3g (-)-tartaric acid and 90ml methanol, heat on a water bath to near boiling (about 60°C), and stir to dissolve the tartaric acid. Then, 5 g of R-α-phenylethylamine was slowly added under stirring. Placed for more than 24h, white prismatic crystals. Suction filter, wash with a small amount of cold methanol, and dry to obtain R-amine·(-)-tartrate.

[0029] [a] 5 D =-10.1° (c=1.30, CH 3 OH); 1 HNMR (300MHz, CD 3 OD, 27℃), δ(ppm)=7.38~7.48(m, 5H), 4.89(s, 5H), 4.43~4.48(m, 1H), 4.40(s, 2H), 1.62~1.64(d, J =5.16,3H), 13 CNMR, 20.80(x2), 52.27, 74.20, 127.69, 130.04, 130.24, 139.89, 177.07, .IR: 3...

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Abstract

The invention discloses a making method of chiral (R / S)-a-phenethylamine (+ / -)-tartrate, which is reacted by R or S-patterned phenethylamine and (+) or (-) tartaric acid, wherein the chiral salt can be catalyst in the asymmetrical reaction with not less than 99%.

Description

1. Technical field [0001] The present invention relates to a new application of a known compound, in particular to a new application of a phenethylamine salt, specifically a chiral (R / S)-a-phenylethylamine (+ / -)-tartrate in New uses in asymmetric catalytic reactions. 2. Background technology [0002] Cyanohydrin compounds are important intermediates in organic synthesis, especially chiral aryl cyanohydrin is an important pharmaceutical intermediate. Therefore, the addition reaction of carbonyl, especially aromatic aldehyde, with cyanide or nitrile has been extensively studied. [0003] Chiral cyanohydrins can be separated from racemates, but the operation is complicated and the efficiency is low. If a chiral catalyst is used, it can be obtained directly by synthesis. 3. Contents of the invention [0004] The invention aims at preparing chiral target products for the addition reaction of aromatic aldehydes and cyanides or nitriles, and the technical problem to be solved ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18B01J31/02B01J31/04
Inventor 罗梅
Owner HEFEI UNIV OF TECH
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