Production Method 1

1418193-04-0

955028-88-3

955029-44-4

Reaction Conditions

Reference

Preparation of pyridinyl pyrimidinyl piperidine compounds as GPR119 modulators for therapy

, World Intellectual Property Organization, , ,

Production Method 2

211108-50-8

955028-88-3

955029-44-4

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  2 h, 0 °C; 0 °C → rt
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Preparation of imidazopyrazole derivatives for use as GPR119 inhibitors

, World Intellectual Property Organization, , ,

Production Method 3

211108-50-8

955028-88-3

Reaction Conditions

Reference

Quinazolinones as PARP14 inhibitors and their preparation

, World Intellectual Property Organization, , ,

Production Method 4

955028-88-3

Reaction Conditions

Reference

Gpr 119 modulators

, United States, , ,

Production Method 5

955028-88-3

Reaction Conditions

Reference

Preparation of pyrimidine compounds as therapeutic GPR 119 modulators

, World Intellectual Property Organization, , ,

Production Method 6

211108-50-8

955028-88-3

955029-44-4

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  2 h, rt
1.2 Reagents: Methanol ,  Water ;  rt

Reference

Heterocyclic-substituted pyrrolopyridines and pyrrolopyrimidines as JAK inhibitors and their preparation

, World Intellectual Property Organization, , ,

Production Method 7

211108-50-8

955028-88-3

955029-44-4

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  2 h, 0 °C; 0 °C → rt
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Preparation of ring-fused pyrrolidines, pharmaceutical compositions containing them, and their use as GPR119 modulators

, World Intellectual Property Organization, , ,

Production Method 8

24424-99-5

22282-73-1

955028-88-3

Reaction Conditions

1.1 Reagents: Hexamethyldisilazane Solvents: Tetrahydrofuran ;  50 psi, 80 °C; 1 h, 80 °C; 80 °C → rt
1.2 Catalysts: p-Toluenesulfonic acid monohydrate ;  24 h, 200 psi, rt → 105 °C

Reference

Preparation of pyrimidine compounds as therapeutic GPR 119 modulators

, World Intellectual Property Organization, , ,

Production Method 9

211108-50-8

955028-88-3

Reaction Conditions

1.1 Reagents: Lithium tri-sec-butylborohydride Solvents: Tetrahydrofuran ;  overnight, 0 °C → rt
1.2 Reagents: Sodium hydroxide ,  Hydrogen peroxide Solvents: Methanol ,  Water ;  rt → 0 °C; 30 min, 0 °C; 2 h, 0 °C

Reference

Discovery of a novel class of imidazo[1,2-a]pyridines with potent PDGFR activity and oral bioavailability

Hicken, Erik J.; Marmsater, Fred P.; Munson, Mark C.; Schlachter, Stephen T.; Robinson, John E.; et al, ACS Medicinal Chemistry Letters, 2014, 5(1), 78-83

Production Method 10

211108-50-8

955028-88-3

Reaction Conditions

1.1 Reagents: Lithium tri-sec-butylborohydride Solvents: Tetrahydrofuran ;  0 °C; 4 h, 0 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  overnight, rt

Reference

Preparation of fluorinated piperidine derivatives as 5-HT2B receptor antagonists for treatment of pulmonary arterial hypertension, pulmonary fibrosis or irritable bowel syndrome

, World Intellectual Property Organization, , ,

Production Method 11

24424-99-5

913574-95-5

955028-88-3

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Methanol ;  3 h, 8 atm, rt

Reference

Preparation of N-containing heterocyclic derivatives as renal outer medullary potassium channel inhibitors

, World Intellectual Property Organization, , ,

Production Method 12

24424-99-5

913574-95-5

955028-88-3

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium dihydroxide Solvents: Methanol ;  35 psi, rt

Reference

Pyridazinones as tyrosine kinase inhibitors and their preparation and use in the treatment of cancer

, World Intellectual Property Organization, , ,

Production Method 13

955028-88-3

Reaction Conditions

Reference

Pyrazine substituted pyrrolopyridines as inhibitors of jak and pdk1

, United States, , ,

Production Method 14

955028-88-3

Reaction Conditions

Reference

Imidazo-pyrazoles as gpr119 inhibitors

, United States, , ,

Production Method 15

955028-88-3

Reaction Conditions

Reference

Preparation of tetraaza-cyclopenta[a]indenyl derivatives as muscarinic M1 mediators

, India, , ,

Production Method 16

955028-88-3

Reaction Conditions

Reference

Preparation of carboxamide, sulfonamide and amine compounds useful in treatment and prevention of diseases

, World Intellectual Property Organization, , ,

Production Method 17

955028-88-3

Reaction Conditions

Reference

JAK kinase inhibitors for the treatment of myeloproliferative disorders or cancer

, World Intellectual Property Organization, , ,

Production Method 18

955028-88-3

Reaction Conditions

Reference

Novel diazepane derivatives as CCR2 antagonists and their preparation, pharmaceutical compositions an use in the treatment of diseases

, United States, , ,

Production Method 19

211108-50-8

955028-88-3

955029-44-4

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  2 h, 0 °C; 0 °C → rt
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Preparation of 4-(5-cyanopyrazol-1-yl)-piperidine derivatives as GPR119 modulators useful in the treatment of metabolic diseases

, World Intellectual Property Organization, , ,

Production Method 20

211108-50-8

955028-88-3

955029-44-4

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  2 h, 0 °C; 0 °C → rt

Reference

Preparation of pyrimidine compounds as therapeutic GPR 119 modulators

, World Intellectual Property Organization, , ,

tert-butyl cis-3-fluoro-4-hydroxypiperidine-1-carboxylate Raw materials

• Di-tert-butyl dicarbonate
• Tert-butyl 3-fluoro-4-oxopiperidine-1-carboxylate
• (3S)-Tert-butyl 3-fluoro-4-hydroxypiperidine-1-carboxylate
• 3-Fluoropyridin-4-ol
• benzyl cis-3-fluoro-4-hydroxy-piperidine-1-carboxylate

tert-butyl cis-3-fluoro-4-hydroxypiperidine-1-carboxylate Preparation Products

• tert-butyl cis-3-fluoro-4-hydroxypiperidine-1-carboxylate (955028-88-3)
• tert-butyl trans-3-fluoro-4-hydroxypiperidine-1-carboxylate (955029-44-4)

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tert-butyl cis-3-fluoro-4-hydroxypiperidine-1-carboxylate (CAS No. 955028-88-3): A Versatile Building Block in Modern Organic Synthesis

The compound tert-butyl cis-3-fluoro-4-hydroxypiperidine-1-carboxylate (CAS No. 955028-88-3) is a highly specialized piperidine derivative that has garnered significant attention in the field of organic chemistry and pharmaceutical research. Its unique structural features, including a fluorine substituent and a hydroxyl group in the cis-configuration, make it a valuable intermediate for the synthesis of complex molecules. This article delves into its properties, applications, and relevance in contemporary scientific discussions.

One of the most frequently searched topics in organic synthesis revolves around the role of fluorinated compounds in drug discovery. The incorporation of fluorine atoms into organic molecules often enhances their metabolic stability, bioavailability, and binding affinity to biological targets. The tert-butyl cis-3-fluoro-4-hydroxypiperidine-1-carboxylate exemplifies this trend, as its fluoro-hydroxypiperidine scaffold is a sought-after motif in the design of bioactive molecules. Researchers are particularly interested in how this compound can be leveraged to develop new therapeutic agents with improved efficacy and safety profiles.

Another hot topic in the scientific community is the use of chiral building blocks for asymmetric synthesis. The cis-configuration of the 3-fluoro-4-hydroxypiperidine moiety in this compound provides a stereochemical handle that can be exploited to construct enantiomerically pure products. This is crucial for the development of chiral drugs, where the spatial arrangement of atoms can significantly influence pharmacological activity. The tert-butyl protecting group further enhances the compound's utility by offering a reversible masking strategy for the piperidine nitrogen, a feature often queried in organic synthesis forums.

From a synthetic chemistry perspective, the tert-butyl cis-3-fluoro-4-hydroxypiperidine-1-carboxylate is a versatile reagent. Its applications span the preparation of heterocyclic compounds, peptide mimetics, and small-molecule inhibitors. Recent publications have highlighted its use in the synthesis of kinase inhibitors and GPCR modulators, two classes of compounds that dominate current drug discovery pipelines. The compound's compatibility with a wide range of coupling reactions and catalytic transformations makes it a favorite among medicinal chemists.

In the context of green chemistry, there is growing interest in optimizing the synthesis of tert-butyl cis-3-fluoro-4-hydroxypiperidine-1-carboxylate to minimize waste and reduce the use of hazardous reagents. Questions about scalable synthetic routes and environmentally friendly protocols are increasingly common in search queries, reflecting the industry's shift toward sustainable practices. Researchers are exploring catalytic fluorination and biocatalytic methods as potential avenues to achieve these goals.

The compound's relevance extends to academic research as well. It serves as a model substrate for studying stereoselective reactions and conformational analysis of fluorinated piperidines. These studies are essential for advancing our understanding of molecular recognition and structure-activity relationships, topics that frequently appear in scientific literature and conference presentations.

In summary, tert-butyl cis-3-fluoro-4-hydroxypiperidine-1-carboxylate (CAS No. 955028-88-3) is a multifaceted compound with broad applications in drug discovery, asymmetric synthesis, and materials science. Its structural uniqueness and synthetic versatility align with current trends in fluorine chemistry and sustainable synthesis, making it a subject of ongoing interest for researchers and industry professionals alike.

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• 1174020-40-6(tert-butyl (3S,4R)-3-fluoro-4-hydroxy-piperidine-1-carboxylate)
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