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Processes for preparing 6,7,8-trihydroxy-1-(hydroxymethyl)-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane

A C1-C4, alkyl technology, applied in the field of preparation of Jinggang mycophenolamine and its derivatives, can solve the problems that are not suitable for large-scale industrial production

Inactive Publication Date: 2008-04-02
YUHAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] Methods (5) and (6) also require special production equipment, so they are not suitable for large-scale industrial production

Method used

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  • Processes for preparing 6,7,8-trihydroxy-1-(hydroxymethyl)-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane
  • Processes for preparing 6,7,8-trihydroxy-1-(hydroxymethyl)-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane
  • Processes for preparing 6,7,8-trihydroxy-1-(hydroxymethyl)-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0042] Preparation 1 9-bromo-6,7,8-trihydroxy-1-(hydroxymethyl)-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane

[0043] Add 200ml of an aqueous solution containing 9.3g of N-(benzyloxycarbonyl) Jinggangamine and 250ml of an aqueous solution containing 5.3g of bromine to 100ml of water cooled to 5-10°C within about 1 hour. The reaction mixture was stirred at the same temperature for 1.5 hours, adjusted to pH 6 with sodium bicarbonate, and washed with ethyl acetate. The aqueous solution was concentrated under reduced pressure, and the concentrate was separated and purified with an MCI GelCHP 20P chromatographic column (Mitsubishi Chemical Corporation, Japan, 600 ml). The eluate was concentrated. The resulting residue was crystallized and filtered to give 6.5 g of the title compound.

[0044] 1 H NMR (D 2O, 400MHz) δ4.70 (1H, s), 4.30 (1H, d, J 9.6Hz), 4.14 (1H, d, J 9.6Hz), 4.07 (1H, d, J 13.2Hz), 3.93-3.87 ( 2H, m), 3.69-3.59 (1H, m)

Embodiment 1

[0045] Example 1 6,7,8-trihydroxy-1-hydroxymethyl-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane

[0046] To 400ml water containing 100g 9-bromo-6,7,8-trihydroxyl-1-(hydroxymethyl)-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane and 1.1 g of α,α'-azobisisobutyronitrile and 46.2 g of sodium hypophosphite were added to a suspension of 300 ml of methanol in a mixed solvent. The reaction mixture was stirred at 80-85°C for 3 hours and then cooled to 50-60°C. The reaction mixture was filtered to remove insoluble matter, and the filtrate was concentrated under reduced pressure. To the obtained residue was added 500 ml of methanol, followed by reflux for 30 minutes. The reaction mixture was stirred at room temperature for 1 hour and then filtered. The resulting crystals were dried under reduced pressure to obtain 67 g of white crystals of the title compound.

[0047] 1 H NMR (D 2 O, 400MHz) δ3.82 (1H, d, J 12.4Hz), 3.69-3.63 (3H, m), 3.60 (1H, d, J 9.2Hz), 3.49 (1H, t, J 9.2Hz), 2.15 ( 1H, dd, J ...

Embodiment 2

[0048] Example 2 6,7,8-trihydroxy-1-(hydroxymethyl)-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane

[0049] To the suspension of 400ml water containing 100g 9-bromo-6,7,8-trihydroxyl-1-(hydroxymethyl)-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane In the liquid, add 1.1g α, α'-azobisisobutyronitrile and 46.2g sodium hypophosphite. The reaction mixture was stirred at 80-85°C for 3 hours and then cooled to 50-60°C. The reaction mixture was filtered to remove insoluble matter, and the filtrate was concentrated under reduced pressure. To the obtained residue was added 500 ml of methanol, followed by reflux for 30 minutes. The reaction mixture was stirred at room temperature for 1 hour and then filtered. The obtained crystals were dried under reduced pressure to obtain 68.3 g of white crystals of the title compound.

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PUM

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Abstract

Provided are processes for preparing 6,7,8-trihydroxy-1-(hydroxymethyl)-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane and processes for preparing valiolamine or its derivative using the same.

Description

technical field [0001] The invention relates to a preparation method of 6,7,8-trihydroxy-1-hydroxymethyl-3-oxo-2-oxa-4-azabicyclo[3.3.1]nonane. The invention also relates to a method for preparing Jinggang mycosanolamine and its derivatives. Background technique [0002] Jinggang mycophenolamine, the chemical name is: (1S)-(1-(OH),2,4,5 / 1,3)-5-amino-1-C-(hydroxymethyl)-1,2,3 , 4-cyclohexanethritol, which has the activity of inhibiting α-glucosidase (US Patent 4,446,319). In addition, the N-substituted derivatives of mycosamine, such as N-(1,3-dihydroxy-2-propyl) mycosamine, also have α-glucosidase inhibitory activity (US Patent No. 4,701,559). Jinggang Mycosamine and N-(1,3-dihydroxy-2-propyl) Jinggang Mycosamine have the effect on prevention and treatment of symptoms of hyperglycemia and various diseases caused by hyperglycemia, such as diabetes, obesity and hyperlipidemia. very good result. Mycoamine and N-(1,3-dihydroxy-2-propyl) mycoamine are represented by the follo...

Claims

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Application Information

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IPC IPC(8): C07H3/02
CPCC07H3/02
Inventor 李泰五权景灿
Owner YUHAN
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