3-[(3R,4S)-3,4-dimethylpiperidin-4-yl]phenol

Base Information

• Chemical Name: 3-[(3R,4S)-3,4-dimethylpiperidin-4-yl]phenol
• CAS No.: 145678-87-1
• Molecular Formula: C13H19NO
• Molecular Weight: 205.30
• Hs Code.: 2933399990
• DSSTox Substance ID: DTXSID90595339
• Wikidata: Q82490339
• Mol file: 145678-87-1.mol

Synonyms:3-[(3R,4S)-3,4-dimethylpiperidin-4-yl]phenol;145678-87-1;1980007-99-5;3-(trans-3,4-Dimethylpiperidin-4-yl)phenol;119193-27-0;3-((3R,4S)-3,4-Dimethylpiperidin-4-yl)phenol;(+)-3-[(3R,4S)-3,4-Dimethylpiperidin-4-yl]phenol;(+)-(3s,4s)-3,4-Dimethyl-4-(3-hydroxyphenyl)piperidine;59381-63-4;SCHEMBL971917;DTXSID90595339;PHENOL,3-[(3S,4S)-3,4-DIMETHYL-4-PIPERIDINYL]-;AKOS015910341;F18408;3,4-cis-Dimethyl-4-(3-hydroxyphenyl)piperidine;trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine

Chemical Property of 3-[(3R,4S)-3,4-dimethylpiperidin-4-yl]phenol

Chemical Property:

• Boiling Point: 335.464 °C at 760 mmHg
• Flash Point: 115.716 °C
• PSA: 32.26000
• Density: 1.009 g/cm³
• LogP: 2.60810
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 205.146664230
• Heavy Atom Count: 15
• Complexity: 219

Purity/Quality:

97% ^*data from raw suppliers

(-)-(3S,4S)-3,4-Dimethyl-4-(3-hydroxyphenyl)piperidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CNCCC1(C)C2=CC(=CC=C2)O
• Isomeric SMILES: C[C@H]1CNCC[C@]1(C)C2=CC(=CC=C2)O
• General Description: (+)-(3R,4S)-3,4-DIMETHYL-4-(3-HYDROXYPHENYL)PIPERIDINE is a potent and peripherally selective opioid antagonist with high affinity for μ-opioid receptors (Ki = 0.77 nM), demonstrating significant potential for treating gastrointestinal motility disorders. Its selective distribution to peripheral receptors minimizes central side effects, making it a promising candidate for clinical investigation. (+)-(3R,4S)-3,4-DIMETHYL-4-(3-HYDROXYPHENYL)PIPERIDINE exhibits strong antagonist activity following both parenteral and oral administration, highlighting its therapeutic utility.

Technology Process of 3-[(3R,4S)-3,4-dimethylpiperidin-4-yl]phenol

There total 14 articles about 3-[(3R,4S)-3,4-dimethylpiperidin-4-yl]phenol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

1,3-dimethyl-4-[3-(propan-2-yloxy)phenyl]-4-piperidinol (145340-44-9,172376-39-5) → (-)-3(S),4(S)-dimethyl-4-(3-hydroxyphenyl)piperidine (145678-87-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: ethyl acetate

1.2: (+)-diethyl ditoluyltartrate

2.1: decahydronaphthalene / Heating

3.1: n-BuLi

4.1: phenyl chloroformate

5.1: HBr; AcOH

With n-butyllithium; hydrogen bromide; acetic acid; phenyl chloroformate; In ethyl acetate; decalin;

DOI:10.1021/jm030094y

Reference yield:

1,3-dimethyl-4-piperidinone (4629-80-5) → (-)-3(S),4(S)-dimethyl-4-(3-hydroxyphenyl)piperidine (145678-87-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: tetrahydrofuran

2.1: ethyl acetate

2.2: (+)-diethyl ditoluyltartrate

3.1: decahydronaphthalene / Heating

4.1: n-BuLi

5.1: phenyl chloroformate

6.1: HBr; AcOH

With n-butyllithium; hydrogen bromide; acetic acid; phenyl chloroformate; In tetrahydrofuran; ethyl acetate; decalin;

DOI:10.1021/jm030094y

Reference yield:

Carbonic acid ethyl ester (3R,4S)-4-(3-isopropoxy-phenyl)-1,3-dimethyl-piperidin-4-yl ester (149541-62-8) → (-)-3(S),4(S)-dimethyl-4-(3-hydroxyphenyl)piperidine (145678-87-1)

Guidance literature:

Multi-step reaction with 4 steps

1: decahydronaphthalene / Heating

2: n-BuLi

3: phenyl chloroformate

4: HBr; AcOH

With n-butyllithium; hydrogen bromide; acetic acid; phenyl chloroformate; In decalin;

DOI:10.1021/jm030094y

upstream raw materials:

1,3-dimethyl-4-piperidinone

(S)-1,2,3,6-tetrahydro-1,3-dimethyl-4-[3-(1-methylethoxy)phenyl]pyridine

(3S,4S)-4-(3-Isopropoxy-phenyl)-1,3,4-trimethyl-piperidine

Carbonic acid ethyl ester (3R,4S)-4-(3-isopropoxy-phenyl)-1,3-dimethyl-piperidin-4-yl ester

Downstream raw materials:

2‐((S)‐2‐benzyl‐3‐((3S,4S)‐4‐(3‐hydroxyphenyl)‐3,4‐dimethylpiperidin‐1‐yl)propanamido)acetic acid

2‐((R)‐2‐benzyl‐3‐((3S,4S)‐4‐(3‐hydroxyphenyl)‐3,4‐dimethylpiperidin‐1‐yl)propanamido)acetic acid

LY 255265

Refernces

Discovery of a Potent, Peripherally Selective trans-3,4-Dimethyl-4-(3-hydroxyphenyl)piperidine Opioid Antagonist for the Treatment of Gastrointestinal Motility Disorders

10.1021/jm00041a003

The study focuses on the development of a peripherally selective opioid antagonist for treating gastrointestinal (GI) motility disorders. The researchers conducted structure-activity relationship (SAR) studies on N-substituted-trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines to identify a potent antagonist with high affinity for opioid receptors and selectivity for peripheral receptors. The compound 3 (LY246736) was discovered, which has high affinity for opioid receptors (Ki = 0.77, 40, and 4.4 nM for μ, κ, and δ receptors, respectively), is a potent μ receptor antagonist following parenteral and oral administration, and distributes selectively to peripheral receptors. This makes compound 3 suitable for clinical investigation of μ opioid receptor involvement in GI motility disorders. The study involved various chemicals, including the parent compound 2, the quaternary opioid antagonist naloxone methiodide (1), and the synthesized compounds 3, 10, 11, 12, 13, 14, and 15. The synthesis process and the roles of these chemicals in achieving the desired antagonist properties are detailed in the study.

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