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(S)- or (R)-epsilon-(2-alkyloxyethyl)-epsilon-caprolactone, preparation method and application thereof

A technology of alkoxyethyl and caprolactone, applied in the preparation of carboxylate/lactone, organic chemistry, etc., can solve the problems of low space-time yield and complexity of bioreduction, achieve mild conditions, simple steps, and easy industrialization Effect

Inactive Publication Date: 2012-09-05
SHANGHAI INST OF PHARMA IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Bezbarua etc. [Bezbarua.M.S, Synthesis, 11,1289 (1996)] obtain its single optical isomer by the carbonyl in the stereoselective reduction of 6-oxo-8-alkoxy octanoate by biological method, but The shortcoming of this method is that the space-time yield of bioreduction is low, and the preparation [Shojiro Y., Mitsuo N., Yakugaku Zasshi, 80,1170 (1960) of used raw material 6-oxo-8-alkoxy octanoate; Bezbarua M.S , Synthesis, 11, 1289 (1996)] is more complex

Method used

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  • (S)- or (R)-epsilon-(2-alkyloxyethyl)-epsilon-caprolactone, preparation method and application thereof
  • (S)- or (R)-epsilon-(2-alkyloxyethyl)-epsilon-caprolactone, preparation method and application thereof
  • (S)- or (R)-epsilon-(2-alkyloxyethyl)-epsilon-caprolactone, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～5

[0038] Table 1 provides examples 1 to 5 of the compound (S) or (R)-ε-(2-alkoxyethyl)-ε-caprolactone whose structure is shown in formula I:

[0039] Formula I

Embodiment 1

[0042] Method Example 1 Preparation of clathrate (S)-2-(2-methoxyethyl)cyclohexanone·2(S,S)-TADDOL

[0043] 34 g of (2S, 3S)-α, α, α′, α′-tetraphenyl-1,4-dioxaspiro-[4.5]decane-2,3-dimethanol ((S, S)- TADDOL) into a 500ml eggplant-shaped bottle, add 220ml methanol to the bottle, and pour 110ml of deionized water with 5 grams of sodium hydroxide into the eggplant-shaped bottle, and finally add 5 grams of 2-(2-methoxyethyl ) cyclohexanone, after stirring at room temperature for two days, add 200ml of saturated aqueous ammonium chloride solution, extract 50ml × 3 with isopropyl ether, and evaporate the solvent under reduced pressure after drying to obtain 38 grams of white solid, most of which are (S) -2-(2-Methoxyethyl)cyclohexanone·2(S,S)-TADDOL inclusion compound (containing a small amount of TADDOL).

Embodiment 2

[0044] Method Example 2 Preparation of clathrate (R)-2-(2-methoxyethyl)cyclohexanone·2(R,R)-TADDOL

[0045] Mix 1.5 g of 2-(2-methoxyethyl)cyclohexanone with 10 g of (2R,3R)-α,α,α′,α′-tetraphenyl-1,4-dioxaspiro-[4.5] Decane-2,3-dimethanol ((R, R)-TADDOL) was put into a 250ml eggplant-shaped bottle, 70ml of methanol was poured into the bottle, 1.6 grams of sodium hydroxide was dissolved in 70ml of deionized water and poured into the eggplant-shaped bottle bottle, stirred at room temperature for two days, added 50ml of saturated ammonium chloride aqueous solution, extracted 25ml×3 with isopropyl ether, dried and evaporated the solvent under reduced pressure to obtain (R)-2-(2-methoxyethyl)cyclohexanone · 11 grams of 2(R,R)-TADDOL clathrate (containing a small amount of TADDOL).

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Abstract

The invention discloses novel compound (S)-or(R)-Epsilon-(2-alcoxyl ethide)-Epsilon-caprolactone showed in the formula 1 and the preparation method thereof, and an application in synthesizing (S) or (R)-6-hydroxide radical-8-alkoxyl octanoic acid or ester thereof used as important reaction intermediate. In the formula 1, R1 is the alkyl of C1-C4 or phenethyl-C2H4Ph. The invention has the advantages of simple steps, mild condition, effectively transforming racemization 2-(2-alcoxyl ethide) cyclohexanone into (S) or (R)-2-(2-alcoxyl ethide) cyclohexanone which has the relatively high optical purity, and finally Baeyer-Villiger oxidizing (S) or (R)-2-(2-alcoxyl ethide) cyclohexanone to produce the compound showed in the formula 1, with the same shape of the product. The application of the compound of the invention used as the reaction intermediate can simplify the preparation method for (S) or (R)-6-hydroxide radical-8-alkoxyl octanoic acid and the ester thereof, thereby being suitable to the industrial production.

Description

technical field [0001] The present invention relates to a novel compound (S)- or (R)-ε-(2-alkoxyethyl)-ε-caprolactone, its preparation method, and its application as a reaction intermediate. Background technique [0002] (S) or (R)-6-hydroxy-8-alkoxyoctanoic acid or its esters can be used as important chiral intermediates for the preparation of (R)-lipoic acid and its enantiomers. Bezbarua etc. [Bezbarua.M.S, Synthesis, 11,1289 (1996)] obtain its single optical isomer by the carbonyl in the stereoselective reduction of 6-oxo-8-alkoxy octanoate by biological method, but The shortcoming of this method is that the space-time yield of bioreduction is low, and the preparation [Shojiro Y., Mitsuo N., Yakugaku Zasshi, 80,1170 (1960) of used raw material 6-oxo-8-alkoxy octanoate; Bezbarua M.S , Synthesis, 11, 1289 (1996)] is more complicated. [0003] The novel compound (S)- or (R)-ε-(2-alkoxyethyl)-ε-caprolactone disclosed by the present invention can be used as a reaction interm...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D313/04C07C59/125C07C51/09C07C69/708
Inventor 刘娜黄成军周后元
Owner SHANGHAI INST OF PHARMA IND CO LTD
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