Preparation method for L-muscone

A muscone and imine technology is applied in the direction of organic chemical methods, chemical instruments and methods, and preparation of imino compounds. It can solve the problems of cumbersome synthesis of chiral diols, high catalyst costs, and low overall yields. The effect of low cost, high total yield and low price

Active Publication Date: 2019-04-26
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Of these two methods, the former uses the expensive [RuCl 2 (cht)] 2 +(S)-BINAP chiral catalyst, the cost of catalyst is high, and the synthesis of chiral diol is cumbersome and expensive; while the method used by the latter, although the process is simple, the overall yield is low, only 44%
[0005] In summary, there is still a lack of effective methods for the synthesis of levomuscone with high yield and low cost.

Method used

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  • Preparation method for L-muscone
  • Preparation method for L-muscone
  • Preparation method for L-muscone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] In the air, in a 2000mL round bottom flask equipped with a condenser, add 118.15g dehydromusketone (500.0mmol), 89.60g (500.0mmol), 4.305g p-toluenesulfonic acid (25mmol) and ethyl acetate (1000.0mL), after nitrogen replacement for 20 minutes, react at 80°C for 4h under nitrogen protection. The reaction solution was cooled to room temperature and washed with Na 2 CO 3 Saturated solution (1000.0mL) and NaCl saturated solution (1000.00mL) were washed twice respectively, anhydrous NaCl 2 SO 4 After drying, the solvent was evaporated with a rotary evaporator, and the liquid phase analysis gave 192.92 g of unsaturated imine, with a yield of 97.07%.

[0048] In the glove box, in a 500mL stainless steel autoclave, add 99.37g of unsaturated imine (250mmol), [Ir(COD)Cl] 2 (0.1mol%, relative to unsaturated imine), triphenylphosphine (100.0mol%, relative to iridium metal precursor) and ethanol (200mL) to seal the autoclave, out of the glove box, and replace nitrogen with hydr...

Embodiment 2

[0055] In the air, in a 2000mL round bottom flask equipped with a condenser, add 118.15g dehydromusketone (500.0mmol), 72.71g (600mmol), 0.05g hydrochloric acid (HCl 37wt%, 0.5mmol) and toluene (100.0mL), after nitrogen replacement for 20 minutes, react at 100°C for 8h under nitrogen protection. The reaction solution was cooled to room temperature and washed with Na 2 CO 3 Saturated solution (1000.0mL) and NaCl saturated solution (1000.00mL) were washed twice respectively, anhydrous NaCl 2 SO 4 After drying, the solvent was evaporated with a rotary evaporator, and the liquid phase analysis gave 163.14 g of unsaturated imine, with a yield of 96.11%.

[0056] In the glove box, in a 500mL stainless steel autoclave, add 84.87g of unsaturated imine (250mmol), [Ir(acac)(CO) 2 ] (5.0 mol%, relative to the unsaturated imine), 1,2-bis(diphenylphosphino)methane (120.0 mol%, relative to the iridium metal precursor) and tetrahydrofuran (200 mL) The autoclave was sealed, and the glove...

Embodiment 3

[0059] In the air, in a 2000mL round bottom flask equipped with a condenser, add 118.15g dehydromusketone (500.0mmol), 59.70g (400.0mmol), 9.8g of sulfuric acid (100mmol) and acetonitrile (250.0mL), after nitrogen replacement for 20 minutes, react at 40°C for 1h under nitrogen protection. The reaction solution was cooled to room temperature and washed with Na 2 CO 3 Saturated solution (1000.0mL) and NaCl saturated solution (1000.00mL) were washed twice respectively, anhydrous NaCl 2 SO 4 After drying, the solvent was evaporated with a rotary evaporator, and the liquid phase analysis gave 137.02 g of unsaturated imine, with a yield of 93.2%.

[0060] In the glove box, in a 500mL stainless steel autoclave, add 91.89g of unsaturated imine (250mmol), [Ir(COD)OMe] 2 (0.5mol%, relative to the unsaturated imine), 1,2-bis(diphenylphosphino)benzene (150.0mol%, relative to the iridium metal precursor) and methanol (200mL) to seal the autoclave, out of the glove box , replace nitro...

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Abstract

The invention provides a preparation method for L-muscone. Dehydrogenated muscone is taken as a starting material, chiral amine is taken as an inducer, homogeneous phase iridium is taken as a catalyst, hydrogen is taken as a reducing agent, and the L-muscone product is synthesized through imine synthesis, asymmetric hydrogenation and hydrolysis reaction. The homogeneous phase iridium catalyst usedin the method has low dose and low cost; the synthetic route has high total yield and few three wastes and is suitable for industrial production of L-muscone.

Description

technical field [0001] The invention belongs to the field of flavors and fragrances and pharmaceutical engineering, and in particular relates to a method for preparing L-muscone. Background technique [0002] Muscone, that is, 3-methylcyclopentadecanone, is the main source of the rare fragrance of natural musk. It can play an excellent role in fixing fragrance, setting off and mellowing in essence, and is extremely precious in perfumery. At the same time, muscone also has the functions of resuscitating, warding off foulness, dredging collaterals, and dissipating stasis, and can be used to treat mainly stroke, phlegm syncope, convulsions, nausea and depression, sudden pain in trusted subordinates, traumatic injuries, carbuncle and swelling. Muscone has a chiral center, and natural muscone is in the left-handed configuration, while the synthetic muscone is basically a racemate, that is, an equal mixture of L-musketone and D-musketone. Levothyrone is the main medicinal active ...

Claims

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Application Information

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IPC IPC(8): C07C45/42C07C49/385
CPCC07B53/00C07C45/42C07C249/02C07C2601/18C07B2200/07C07C251/20C07C49/385
Inventor 于斌成黄文学沈稳谢硕
Owner WANHUA CHEM GRP CO LTD
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