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Preparation method of 3-aminomethyl oxetane and its organic acid salts

A technology of aminomethyl oxetane and oxetane, which is applied in the field of preparation of 3-aminomethyl oxetane and organic acid salts thereof, and can solve the problems of unsuitable amplification and the like

Active Publication Date: 2013-01-16
WUXI APPTEC (TIANJIN) CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It mainly solves the problem that the existing preparation method is not suitable for enlargement. The present invention uses the method of catalytic hydrogenation reduction to obtain 3-aminomethyloxetane by one-step reduction, and tries to synthesize its oxalate and acetate

Method used

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  • Preparation method of 3-aminomethyl oxetane and its organic acid salts
  • Preparation method of 3-aminomethyl oxetane and its organic acid salts
  • Preparation method of 3-aminomethyl oxetane and its organic acid salts

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 : Preparation of 3-(nitromethane)oxetan-3-ol

[0033]

[0034] Operation steps: In a 250 ml single-necked bottle, add nitromethane (36 ml) and 3-oxetanone 1 (3.7 g, 51.3 mmol), triethylamine (70 mg) was added under stirring, and reacted at room temperature for 10 hours. The reaction solution was rotary evaporated in vacuo to remove excess nitromethane to obtain 6.8 grams of light yellow liquid 3-(nitromethane)oxetan-3-ol 2 , the yield is 100%.

[0035] HNMR (CDCl 3 ) δ4.83 (s, 2H), 4.72 (d, J = 8.0 Hz, 2H), 4.60 (d, J = 8.0 Hz, 2H).

Embodiment 2

[0036] Example 2 : Preparation of 3-(nitromethylene)oxetane

[0037]

[0038] In a 1-liter three-neck flask, add dichloromethane (300 ml) and 3-(nitromethane)oxetan-3-ol (6.8 g, 51.3 mmol), and cool to –78°C with a dry ice acetone bath . Triethylamine (15.6 g, 154 mmol) was then added dropwise, followed by the slow addition of methanesulfonyl chloride (11.8 g, 104 mmol) in dichloromethane (80 ml) dropwise over 3 hours. After the addition was complete, the reaction was continued to stir at -78°C for 2 hours, then returned to room temperature and stirred for 12 hours. The reaction solution was quenched by pouring into ice water, and extracted with dichloromethane. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate and filtered. After distilling off the solvent under reduced pressure, the filtrate was purified by column chromatography. The eluent is petroleum ether: ethyl acetate = 15:1. Finally, 3.8 g of white solid product was obtai...

Embodiment 3

[0040] Example 3 : Preparation of 3-Aminomethyloxetane Oxalate (Palladium Hydroxide on Carbon and Methanol, Room Temperature, 1 Atm of Hydrogen)

[0041]

[0042] Operation steps: 3-(nitromethylene)oxetane 3 (0.88 g, 7.7 mmol) and 0.3 g of palladium hydroxide on carbon (10% by mass) were added to the reaction flask, 20 ml of methanol was added, stirred at room temperature under 1 atmosphere of hydrogen for 48 hours, and then filtered. The filter cake was thoroughly washed with methanol, and the resulting filtrate was evaporated to remove the solvent under reduced pressure to obtain 1.2 g of a colorless liquid (the solvent methanol remained).

[0043] HNMR (MeOD) δ4.80 (t, J= 6.4 Hz, 2H), 4.40 (t, J= 6 Hz, 2H), 3.05 (m, 1H), 2.97 (t, J= 7.2 Hz, 2H).

[0044] Dissolve the above liquid in 10 ml of tert-butyl methyl ether, then add anhydrous oxalic acid (0.34 g, 3.8 mmol) solution dissolved in about 2 ml of ethanol to the above solution, immediately a white solid precipitate...

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Abstract

The invention discloses a preparation method of 3-aminomethyl oxetane and its oxalate and acetate, mainly solving the problem of existing preparation method is not suitable for large scale production. The method disclosed herein is characterized by using 3-oxacyclobutanone as a starting material, reacting the starting material with nitromethane in alkali condition with the effect of methanesulfuryl chloride to obtain 3-(nitromethylene)oxetane; then under the effect of activated carbon supported palladium hydroxide and hydrogen, reducing to obtain 3-aminomethyl oxetane, and then reacting with oxalic acid or acetic acid to form salts. The total yield is 51%.

Description

Technical field [0001] The present invention involves the preparation method of 3-amino-based oxygenytane and its organic acid, and specially involves the preparation method of 3-ammonia methyl oxygen and its oxalate / acetate. Background technique [0002] The oxygen cycle -buttane compounds occupy an important position in chemical synthetic drugs with their unique structure and properties, and they are often found in natural products.The oxygenic alkane compound contains oxygen atoms with strong electrical negativeness, which makes it have greater polarity and help reduce the lipophytic of the drug molecules.The ring rigid structure of the oxygenyxane compound has enough volume to occupy the cavity.In addition, its stable chemical properties have greatly improved the metabolic stability of drug molecules containing this structure.As or replace similar medicinal group units (such as the second foundation and the base of the cymbals) that can cause changes in the properties of PKA,...

Claims

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Application Information

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IPC IPC(8): C07D305/06C07C55/07C07C53/10C07C51/41
Inventor 甘伟彭宣嘉蔡亚仙董径超吴颢马汝建陈曙辉
Owner WUXI APPTEC (TIANJIN) CO LTD
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