3-((3R,4R)-1-((S)-3-cyclohexyl-3-hydroxypropyl)-3,4-dimethylpiperidin-4-yl)phenol

Base Information

• Chemical Name: 3-((3R,4R)-1-((S)-3-cyclohexyl-3-hydroxypropyl)-3,4-dimethylpiperidin-4-yl)phenol
• CAS No.: 119193-09-8
• Molecular Formula: C22H35 N O2
• Molecular Weight: 345.525
• DSSTox Substance ID: DTXSID201045752
• Nikkaji Number: J381.454H
• Wikipedia: LY-255582
• Wikidata: Q15634042
• Pharos Ligand ID: 5JDPVZBR86UJ
• ChEMBL ID: CHEMBL300662
• Mol file: 119193-09-8.mol

Synonyms:1-(3-hydroxy-3-cyclohexylpropyl)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidine;LY 243670;LY 255265;LY 255582;LY 255609;LY 255610;LY-243670;LY-255265;LY-255582;LY-255609;LY-255610;LY243670;LY255265;LY255582;LY255609;LY255610

Chemical Property of 3-((3R,4R)-1-((S)-3-cyclohexyl-3-hydroxypropyl)-3,4-dimethylpiperidin-4-yl)phenol

Chemical Property:

• PSA: 43.70000
• LogP: 4.26090
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≥15mg/mL
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 345.266779359
• Heavy Atom Count: 25
• Complexity: 409

Purity/Quality:

LY255582 ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CN(CCC1(C)C2=CC(=CC=C2)O)CCC(C3CCCCC3)O
• Isomeric SMILES: C[C@H]1CN(CC[C@@]1(C)C2=CC(=CC=C2)O)CC[C@@H](C3CCCCC3)O

Technology Process of 3-((3R,4R)-1-((S)-3-cyclohexyl-3-hydroxypropyl)-3,4-dimethylpiperidin-4-yl)phenol

There total 14 articles about 3-((3R,4R)-1-((S)-3-cyclohexyl-3-hydroxypropyl)-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: 82.0%

3-[(3R,4R)-3,4-dimethylpiperidin-4-yl]phenol (119193-19-0) + 3-cyclohexyl-3-hydroxypropyl (4-bromobenzene)sulfonate → (+)-1-(3(S)-3-hydroxy-3-cyclohexylpropyl)-3(R),4(R)-dimethyl-4-(3-hydroxyphenyl)piperidine (119193-09-8,120938-72-9)

Guidance literature:

With sodium hydrogencarbonate; In 1,2-dimethoxyethane; for 8h; Heating;

DOI:10.1021/jo951403y

Reference yield:

1-Cyclohexyl-3-[(3R,4R)-4-(3-hydroxy-phenyl)-3,4-dimethyl-piperidin-1-yl]-propan-1-one → (+)-1-(3(S)-3-hydroxy-3-cyclohexylpropyl)-3(R),4(R)-dimethyl-4-(3-hydroxyphenyl)piperidine (119193-09-8,120938-72-9) + LY 255610 (120938-72-9)

Guidance literature:

With sodium tetrahydroborate; In isopropyl alcohol; at 0 ℃; for 1h;

DOI:10.1021/jm00072a002

Reference yield:

3-[(3R,4R)-3,4-dimethylpiperidin-4-yl]phenol (119193-19-0) → (+)-1-(3(S)-3-hydroxy-3-cyclohexylpropyl)-3(R),4(R)-dimethyl-4-(3-hydroxyphenyl)piperidine (119193-09-8,120938-72-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Na₂CO₃ / dimethylformamide / 3 h / Ambient temperature

2: NaBH₄ / propan-2-ol / 1 h / 0 °C

With sodium tetrahydroborate; sodium carbonate; In N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm00072a002

upstream raw materials:

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

(3R,4R)-3,4-dimethyl-4-<3-(1-methylethoxy)phenyl>piperidinecarboxylic acid phenyl ester

(3R,5R)-1,3,4-trimethyl-4-<3-(1-methylethoxy)phenyl>piperidine

1-cyclohexylprop-2-en-1-ol

Downstream raw materials:

Trifluoro-methanesulfonic acid 3-[(3R,4R)-1-((S)-3-cyclohexyl-3-hydroxy-propyl)-3,4-dimethyl-piperidin-4-yl]-phenyl ester

N-{3-[(3R,4R)-1-((S)-3-Cyclohexyl-3-hydroxy-propyl)-3,4-dimethyl-piperidin-4-yl]-phenyl}-2-hydroxy-2-methyl-propionamide

(S)-3-[(3R,4R)-4-(3-Amino-phenyl)-3,4-dimethyl-piperidin-1-yl]-1-cyclohexyl-propan-1-ol

3-[(3R,4R)-1-((S)-3-Cyclohexyl-3-hydroxy-propyl)-3,4-dimethyl-piperidin-4-yl]-benzoic acid methyl ester