# US 11,306,091 B2 · Process for producing fluorinated compounds using alcohol solvent having unsaturated hydrocarbon

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- Number: US 11,306,091 B2
- Document ID: US11306091B2
- Status: Granted
- Kind: B2
- Application number: 16/888,272
- Filed: 2020-05-29
- Published: 2020-12-31
- Granted: 2022-04-19
- Earliest claimed: 2019-06-25
- Assignees: Futurechem Co., Ltd.
- Applicants: Futurechem Co., Ltd
- Inventors: Dae Yoon Chi; Byoung Se Lee; So Young Chu; Hyeon Jin Jeong; Hyeon Seok Kim
- Web page: https://patentgrep.com/patent/US11306091B2

## CPC

- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07D 471/08: Bridged systems
- C07B 59/00: Introduction of isotopes of elements into organic compounds {; Labelled organic compounds per se}
- C07C 41/22: by introduction of halogens; by substitution of halogen atoms by other halogen atoms
- C07C 43/225: containing halogen
- C07C 209/74: by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
- C07C 247/04: being saturated
- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- C07H 1/00: Processes for the preparation of sugar derivatives
- C07B 2200/05: Isotopically modified compounds, e.g. labelled
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

The present invention relates to a process for producing an organofluoro compound including [18F]fluorine, and by using a solvent represented by Formula 1 in nucleophilic fluorination reaction, an organofluoro compound may be prepared at a high yield. In addition, since the solvent has very excellent solubility for a precursor compound, the solvent is suitable for the automated synthesis of 18F-labeled radiopharmaceuticals.

## Claims

### Claim 1

A process for producing an organofluoro compound, the process comprising: reacting an organic compound having a leaving group (LG) with a fluoride in a solvent according to below Reaction 3 in a suitable condition,
wherein the organic compound having a leaving group is
the organofluoro compound is
and X− is an ion generated from the leaving group, wherein R6 and R7 form carbocycle with N, and n is an integer of 0 to 6, wherein the solvent has the following Formula 1:
in Formula 1, R1and R2 are each a methyl group; and R3 is ethenyl or ethynyl, and wherein the fluoride is a [18F] fluoride, and is provided as a component of a phase transfer catalyst.

### Claim 2 (depends on 1)

The process for producing an organofluoro compound according to claim 1, wherein the reaction is performed for 5 minutes to 60 minutes.

### Claim 3 (depends on 1)

The process for producing an organofluoro compound according to claim 1, wherein the reaction is performed in a temperature range of 60° C. to 160° C.

### Claim 4 (depends on 1)

The process for producing an organofluoro according to claim 1, wherein the organofluoro compound is [18F]fluoropropylcarbomethoxytropane ([18F]FP-CIT) having the following Formula 3:

### Claim 5 (depends on 1)

The process for producing an organofluoro compound according to claim 1, wherein X− is an ion of a halo group or is a group having the following Formula 2:
wherein in Formula 2, R4 is hydrogen, linear or branched, unsubstituted or substituted C1-10alkyl, unsubstituted or substituted C6-10aryl, or unsubstituted or substituted C6-10aryl C1-10alkyl, and the substituted alkyl, aryl and aryl alkyl are each independently modified with one or more substituents selected from the group consisting of linear or branched C1-5alkyl, linear or branched C1-5alkoxy, a halo group, an amine group, a nitro group, a nitrile group and a hydroxyl group.

### Claim 6 (depends on 1)

The process for producing an organofluoro compound according to claim 1, 1, wherein X− is F, Cl, Br−, I−,

### Claim 7 (depends on 1)

The process for producing an organofluoro compound according to claim 1, wherein

### Claim 8 (depends on 1)

The process for producing an organofluoro compound according to claim 1, wherein a source of the fluoride is provided as Kryptofix 222 -K [18 F].