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Synthetic method for fluoromethylation of halogenated alcohols

A technology of fluoromethylation and halomethyl ether, applied in the field of fluoromethylation of haloalcohols, can solve the problems of affecting reversible regulation, low yield of fluorinated products, and high cost

Inactive Publication Date: 2003-07-23
ABBOTT LAB INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the exact mechanism of action of sevoflurane has not yet been elucidated, it has recently been found that sevoflurane affects nicotinic acetylcholine receptors by affecting the open and closed states of ion channels at critical or lower concentrations
Sevoflurane may also affect reversible regulation of GABA and glycine receptors
[0011] While the methods described above can be used to prepare some fluorides, these methods can be complex, expensive, and often yield low yields of fluorinated products with considerable by-products

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Bis(1,1,1,3,3,3-hexafluoroisopropoxy)methane was synthesized according to the following reaction scheme I:

[0039] To a solution of 1,1,1,3,3,3-hexafluoroisopropanol (1.5 mL, 15 mmol) and dibromomethane (1.6 mL, 23 mmol) in acetone (5.0 mL) was added K 2 CO 3 (3.15 gm, 23 mmol), the reaction was heated at reflux. After 18 hours the reaction mixture was cooled and filtered to remove solids. The filtrate was distilled to obtain bis(1,1,3,3,3-hexafluoroisopropoxy)methane (1.5 g, 52%). This stable acetal precursor is deprotected and fluorinated to sevoflurane by fluorination methods well known to those skilled in the art.

[0040] Reaction Scheme I

Embodiment 2

[0042] Sevoflurane was synthesized according to the following reaction scheme II:

[0043] K 2 CO 3 (31.5g, 228mmol) and KF (17.5g, 300mmol), the reaction mixture was heated to 100°C. After 18 hours, analysis of the reaction mixture by gas chromatography (GC) showed 92% conversion of HFIP to sevoflurane. The reaction mixture was diluted with water (100 mL), the lower organic layer was separated and distilled to give sevoflurane (12 g, 40%).

[0044] Reaction Scheme II

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Abstract

A method for fluoromethylation of a halogenated alcohol. The method includes refluxing a halogenated alcohol with a dihalomethane under basic conditions in a first solvent to form a halomethyl ether and fluorinating the halomethyl ether in the presence of a fluorinating agent.

Description

field of invention [0001] The present invention relates to a method for the fluoromethylation of haloalcohols, which uses a transient halomethyl ether intermediate. Treatment of the alcohol with dihalomethane under basic conditions produces (transiently) a halomethyl ether intermediate, which reacts with a fluorinating agent to form the desired fluoride. This method can be used to synthesize sevoflurane from hexafluoroisopropanol in a single reaction vessel. A method for the synthesis of sevoflurane from stable acetal precursors is also disclosed. Background of the invention [0002] Anesthetics are biochemical sedatives that affect the vital functions of cells. Anesthetics generally produce analgesia, loss of consciousness, decreased reflex activity, and muscle relaxation with minimal suppression of vital functions. Anesthetics can be gaseous (volatile) or solidified (nonvolatile). Gaseous anesthetics are inhaled and passed through the lungs into the bloodstream, while ...

Claims

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Application Information

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IPC IPC(8): C07C41/16C07C41/22C07C43/12
CPCC07C41/16C07C43/123C07C41/52C07C41/22C07C43/313
Inventor C·比尼尔兹K·V·拉马克里斯纳
Owner ABBOTT LAB INC
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