1174020-46-2 | cis-tert-butyl 4-fluoro-3-hydroxypiperidine-1-carboxylate

CAS:1174020-46-2 | cis-tert-butyl 4-fluoro-3-hydroxypiperidine-1-carboxylate,Description

“Cis-Tert-butyl 4-fluoro-3-hydroxypiperidine-1-carboxylate” is a chemical compound with a molecular formula of C11H21NO3F. It contains a piperidine ring with a fluorine atom attached at the 4 position and a hydroxyl group at the 3 position.

Synthesis Analysis

The synthesis of “cis-Tert-butyl 4-fluoro-3-hydroxypiperidine-1-carboxylate” can be achieved from N-(tert-Butoxycarbonyl)-4-piperidone. Another method involves the reaction of tert-Butyl 3-allyl-4-oxopiperidine-1-carboxylate and its derivatives substituted at the 3-position and in the allylic fragment with L-selectride in anhydrous tetrahydrofuran to give cis isomers in quantitative yield.

Molecular Structure Analysis

The molecular formula of “cis-Tert-butyl 4-fluoro-3-hydroxypiperidine-1-carboxylate” is C10H18FNO3. It has an average mass of 219.253 Da and a monoisotopic mass of 219.127075 Da.

Physical And Chemical Properties Analysis

The compound is a solid or liquid under normal conditions. The storage temperature is 2-8°C in a sealed, dry environment.

Scientific Research Applications

Syntheses and Derivatives

• The research on tert-butyl 4-fluoro-3-hydroxypiperidine-1-carboxylate primarily focuses on its synthesis and derivatives. For instance, Boev et al. (2015) explored the stereoselective synthesis of tert-butyl 3-allyl-4-oxopiperidine-1-carboxylate and its derivatives, demonstrating their potential in forming cis isomers (Boev et al., 2015). Similarly, Toyota et al. (1996) reported a novel method for preparing cis-2-fluorocyclopropane-1-carboxylic acid, starting from tert-butyl acrylate, highlighting the compound's versatility (Toyota et al., 1996).

Enzyme-Catalyzed Kinetic Resolution

• In the field of enzymatic processes, Solymár et al. (2004) achieved a highly enantioselective kinetic resolution of ethyl cis-4 and trans-1-(tert-butoxycarbonyl)-4-hydroxypiperidine-3-carboxylate using Pseudomonas fluorescens lipase (Solymár et al., 2004) .

Chemical Transformations and Catalysis

• Research by Purkayastha et al. (2010) showed that the vinylfluoro group in tert-butyl (2S,5S)-2-tert-butyl-5-(2-fluoroallyl)-3-methyl-4-oxoimidazolidine-1-carboxylate can act as an acetonyl cation equivalent, which is crucial for synthesizing pipecolic acid derivatives (Purkayastha et al., 2010).

Analytical Methodologies

• In analytical chemistry, Leng and Gries (2005) developed a gas chromatographic-high resolution mass spectrometric method for determining various metabolites in human urine, including compounds related to tert-butyl and fluorine components (Leng & Gries, 2005).

Medicinal Chemistry Applications

• In medicinal chemistry, Singh and Umemoto (2011) highlighted the use of 4-fluoropyrrolidine derivatives, including those with tert-butyl groups, as synthons in dipeptidyl peptidase IV inhibitors, showcasing their pharmaceutical relevance (Singh & Umemoto, 2011).

Safety And Hazards

The compound is associated with several hazard statements including H302, H312, H332, indicating that it may be harmful if swallowed, in contact with skin, or if inhaled. Precautionary measures include avoiding contact with skin and eyes, avoiding formation of dust and aerosols, and obtaining special instructions before use.

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