3,4-Piperidinediol, 1,3-dimethyl-4-ethynyl-6-(4-fluorophenyl)-, (3-alpha,4-alpha,6-beta)-

Base Information

• Chemical Name: 3,4-Piperidinediol, 1,3-dimethyl-4-ethynyl-6-(4-fluorophenyl)-, (3-alpha,4-alpha,6-beta)-
• CAS No.: 121368-78-3
• Molecular Formula: C₁₅H₁₈FNO₂
• Molecular Weight: 263.312
• DSSTox Substance ID: DTXSID90153251
• Wikidata: Q83020109
• Mol file: 121368-78-3.mol

Synonyms:3,4-Piperidinediol, 1,3-dimethyl-4-ethynyl-6-(4-fluorophenyl)-, (3-alpha,4-alpha,6-beta)-;3a,4a-Dihydroxy-1e,3e-dimethyl-6e-(4-fluorophenyl)-4e-ethynylpiperidine;(3-alpha,4-alpha,6-beta)-1,3-Dimethyl-4-ethynyl-6-(4-fluorophenyl)-3,4-piperidinediol;121368-78-3;3,4-Piperidinediol, 4-ethynyl-6-(4-fluorophenyl)-1,3-dimethyl-, (3alpha,4alpha,6beta)-;C15-H18-F-N-O2;DTXSID90153251;LS-115164

Chemical Property of 3,4-Piperidinediol, 1,3-dimethyl-4-ethynyl-6-(4-fluorophenyl)-, (3-alpha,4-alpha,6-beta)-

Chemical Property:

• Vapor Pressure: 7.89E-06mmHg at 25°C
• Boiling Point: 360.6°Cat760mmHg
• Flash Point: 171.9°C
• Density: 1.24g/cm³
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 263.13215698
• Heavy Atom Count: 19
• Complexity: 385

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CN(C(CC1(C#C)O)C2=CC=C(C=C2)F)C)O
• Isomeric SMILES: C[C@@]1(CN([C@@H](C[C@@]1(C#C)O)C2=CC=C(C=C2)F)C)O

Technology Process of 3,4-Piperidinediol, 1,3-dimethyl-4-ethynyl-6-(4-fluorophenyl)-, (3-alpha,4-alpha,6-beta)-

There total 4 articles about 3,4-Piperidinediol, 1,3-dimethyl-4-ethynyl-6-(4-fluorophenyl)-, (3-alpha,4-alpha,6-beta)- 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: 98.0%

3a-hydroxy-1e,3e-dimethyl-6e-(4-fluorophenyl)-4-piperidone (36106-54-4,60054-02-6,103021-98-3) + acetylenemagnesium bromide (4301-14-8) → 3a,4a-dihydroxy-1e,3e-dimethyl-6e-(4-fluorophenyl)-4e-ethynylpiperidine (120729-81-9,121368-78-3)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1007/BF00764463

Reference yield: 84.0%

sodium acetylide (1066-26-8) + 3e-hydroxy-1e,3a-dimethyl-6e-(4-fluorophenyl)-4-piperidone (36106-54-4,60054-02-6,103021-98-3) → (3S,4R,6S)-4-Ethynyl-6-(4-fluoro-phenyl)-1,3-dimethyl-piperidine-3,4-diol (120729-81-9,121368-78-3)

Guidance literature:

In diethyl ether; ammonia; for 1h;

DOI:10.1007/BF00764463

Reference yield:

(E)-3-(4-Fluoro-phenyl)-1-(2-methyl-oxiranyl)-propenone (31374-65-9) → 3a,4a-dihydroxy-1e,3e-dimethyl-6e-(4-fluorophenyl)-4e-ethynylpiperidine (120729-81-9,121368-78-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 40 percent / benzene / 1 h / 150 °C

2: 98 percent / tetrahydrofuran / 12 h / 20 °C

In tetrahydrofuran; benzene;

DOI:10.1007/BF00764463

upstream raw materials:

3a-hydroxy-1e,3e-dimethyl-6e-(4-fluorophenyl)-4-piperidone

acetylenemagnesium bromide

(E)-3-(4-Fluoro-phenyl)-1-(2-methyl-oxiranyl)-propenone

sodium acetylide

Downstream raw materials:

(3S,4R,6S)-4-(3-Diethylamino-prop-1-ynyl)-6-(4-fluoro-phenyl)-1,3-dimethyl-piperidine-3,4-diol