142355-83-7

Basic information

• Product Name: tert-butyl 4-(4-hydroxybutyl)piperidine-1-carboxylate
• Synonyms: tert-butyl 4-(4-hydroxybutyl)piperidine-1-carboxylate;4-(4-Hydroxybutyl)piperidine-1-carboxylic acid tert-butyl ester;1-Piperidinecarboxylic acid, 4-(4-hydroxybutyl)-, 1,1-diMethylethyl ester;4-(1-Boc-4-piperidyl)-1-butanol;4-(1-tert-butoxycarbonylpiperidin-4-yl)-butan-1-ol;tert-Butyl 4-(4-hydroxybutyl)
• CAS NO: 142355-83-7
• Molecular Formula: C₁₄H₂₇NO₃
• Molecular Weight: 257.37
• Mol File: 142355-83-7.mol

Chemical Properties

• Boiling Point: 355.1 °C at 760 mmHg
• Flash Point: 168.6 °C
• Appearance: /
• Density: 1.018
• Storage Temp.: 2-8°C
• PKA: 15.18±0.10(Predicted)
• CAS DataBase Reference: tert-butyl 4-(4-hydroxybutyl)piperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 4-(4-hydroxybutyl)piperidine-1-carboxylate(142355-83-7)
• EPA Substance Registry System: tert-butyl 4-(4-hydroxybutyl)piperidine-1-carboxylate(142355-83-7)

Safety Data

• Hazardous Substances Data: 142355-83-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
Tert-butyl 4-(4-hydroxybutyl)piperidine-1-carboxylate is utilized as a key intermediate in the synthesis of biologically active compounds, contributing to the development of new pharmaceuticals. Its presence in the molecular structure of various drug candidates highlights its significance in medicinal chemistry.
Used in Organic Synthesis:
In the field of organic synthesis, tert-butyl 4-(4-hydroxybutyl)piperidine-1-carboxylate is employed as a versatile building block. Its unique structural features allow for the creation of a variety of complex organic molecules, which can be further utilized in different chemical and pharmaceutical applications.
Used in Drug Development:
tert-butyl 4-(4-hydroxybutyl)piperidine-1-carboxylate's potential applications in drug development are attributed to its piperidine structural motif, which is commonly found in pharmaceutical compounds. This makes it a valuable component in the design and synthesis of new drugs with potential therapeutic effects.
Used in the Synthesis of Biologically Active Compounds:
Tert-butyl 4-(4-hydroxybutyl)piperidine-1-carboxylate is recognized for its role in the synthesis of biologically active compounds, which may possess various therapeutic properties. Its intermediate status in these syntheses underscores its importance in the development of novel pharmaceutical agents.

Upstream product

• 142247-38-9 4-[1-(tert-butoxycarbonyl)piperidin-4-yl]butanoic acid 
• 7037-49-2 3-(piperidin-4-yl)propan-1-ol 
• 2629-72-3 4-(3-Hydroxypropyl)pyridine 
• 156185-63-6 N-Boc-piperidin-4-yl-propanol 
• 57614-92-3 4-(piperidin-4-yl)butan-1-ol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 180307-56-6 tert-butyl 4-ethenylpiperidine-1-carboxylate 
• 199475-41-7 4-piperidin-4-yl-butan-1-ol hydrochloride 
• 51052-78-9 4-piperidinylacetic acid 
• 142355-82-6 methyl 4-piperidin-4-yl>butanoate 
• 142355-80-4 methyl 4-piperidin-4-yl>but-2-enoate 
• 157688-46-5 2-(1-(tert-butoxycarbonyl)piperidin-4-yl)acetic acid 
• 142374-19-4 tert-butyl 4-(formylmethyl)piperidine-1-carboxylate 
• 89151-44-0 4-(2-hydroxyethyl)piperidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 142355-81-5 tert-butyl 4-(4-bromobutyl)piperidine-1-carboxylate 
• 142356-28-3 4-{4-[4-((S)-2-Amino-2-carboxy-ethyl)-phenoxy]-butyl}-piperidine-1-carboxylic acid tert-butyl ester 
• 142373-59-9 4-(4-{4-[(S)-2-(Butane-1-sulfonylamino)-2-carboxy-ethyl]-phenoxy}-butyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 142355-84-8 4-{4-[4-((S)-2-Benzyloxycarbonylamino-2-carboxy-ethyl)-phenoxy]-butyl}-piperidine-1-carboxylic acid tert-butyl ester 
• 403857-10-3 3-(2-{(S)-2-(Butane-1-sulfonylamino)-3-[4-(4-piperidin-4-yl-butoxy)-phenyl]-propionyloxy}-4,6-dimethoxy-phenyl)-3-methyl-butyric acid 
• 403857-09-0 4-[4-(4-{2-(butane-1-sulfonylamino)-2-[2-(2-carboxy-1,1-dimethyl-ethyl)-3,5-dimethoxy-phenoxycarbonyl]-ethyl}-phenoxy)-butyl]-piperidine-1-carboxylic acid tert-butyl ester 
• 403857-08-9 1-N-Boc-tirofiban-2-[3-[(1-t-butyl-1,1-dimethylsilyl)oxyl]-1,1-dimethylpropyl]-4,6-dimethoxyphenol 
• 144494-65-5 tirofiban hydrochloride 
• 1025892-42-5 4-{4-[4-(2-Carboxy-ethyl)-phenoxy]-butyl}-piperidine-1-carboxylic acid tert-butyl ester 
• 150022-77-8 Methyl 3-[4-(4-N-t-Butyloxycarbonylpiperidin-4-yl)butyloxyphenyl]propanoate 
• 142373-57-7 4-{4-[4-((S)-2-Amino-2-methoxycarbonyl-ethyl)-phenoxy]-butyl}-piperidine-1-carboxylic acid tert-butyl ester 
• 1026353-54-7 4-{4-[4-((S)-2-Acetylamino-2-carboxy-ethyl)-phenoxy]-butyl}-piperidine-1-carboxylic acid tert-butyl ester 
• 1026809-98-2 4-{4-[4-((S)-2-Carboxy-2-propionylamino-ethyl)-phenoxy]-butyl}-piperidine-1-carboxylic acid tert-butyl ester 
• 155727-70-1 4-{4-[4-((S)-2-Carboxy-2-methanesulfonylamino-ethyl)-phenoxy]-butyl}-piperidine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

A method for one-step synthesis of carboxylic acids with two extended carbon chains from olefins

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In the past 50 years, cross-coupling reactions mediated by transition metals have changed the way in which complex organic molecules are synthesized. The predictable and chemoselective nature of these transformations has led to their widespread adoption across many areas of chemical research. However, the construction of a bond between two sp3-hybridized carbon atoms, a fundamental unit of organic chemistry, remains an important yet elusive objective for engineering cross-coupling reactions. In comparison to related procedures with sp2-hybridized species, the development of methods for sp3-sp3 bond formation via transition metal catalysis has been hampered historically by deleterious side-reactions, such as β-hydride elimination with palladium catalysis or the reluctance of alkyl halides to undergo oxidative addition. To address this issue, nickel-catalysed cross-coupling processes can be used to form sp3-sp3 bonds that utilize organometallic nucleophiles and alkyl electrophiles. In particular, the coupling of alkyl halides with pre-generated organozinc, Grignard and organoborane species has been used to furnish diverse molecular structures. However, the manipulations required to produce these activated structures is inefficient, leading to poor step-and atom-economies. Moreover, the operational difficulties associated with making and using these reactive coupling partners, and preserving them through a synthetic sequence, has hindered their widespread adoption. A generically useful sp3-sp3 coupling technology that uses bench-stable, native organic functional groups, without the need for pre-functionalization or substrate derivatization, would therefore be valuable. Here we demonstrate that the synergistic merger of photoredox and nickel catalysis enables the direct formation of sp3-sp3 bonds using only simple carboxylic acids and alkyl halides as the nucleophilic and electrophilic coupling partners, respectively. This metallaphotoredox protocol is suitable for many primary and secondary carboxylic acids. The merit of this coupling strategy is illustrated by the synthesis of the pharmaceutical tirofiban in four steps from commercially available starting materials.

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