(3S)-3beta-(Methylsulfonyloxymethyl)-4alpha-(4-fluorophenyl)piperidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (3S)-3beta-(Methylsulfonyloxymethyl)-4alpha-(4-fluorophenyl)piperidine-1-carboxylic acid tert-butyl ester
• CAS No.: 200572-34-5
• Molecular Formula: C18H26FNO5S
• Molecular Weight: 387.473
• DSSTox Substance ID: DTXSID201113490
• Nikkaji Number: J1.271.978G
• Mol file: 200572-34-5.mol

Synonyms:SCHEMBL4436548;DTXSID201113490;(3S)-3beta-(Methylsulfonyloxymethyl)-4alpha-(4-fluorophenyl)piperidine-1-carboxylic acid tert-butyl ester;1,1-Dimethylethyl (3S,4R)-4-(4-fluorophenyl)-3-[[(methylsulfonyl)oxy]methyl]-1-piperidinecarboxylate;200572-34-5

Chemical Property of (3S)-3beta-(Methylsulfonyloxymethyl)-4alpha-(4-fluorophenyl)piperidine-1-carboxylic acid tert-butyl ester

Chemical Property:

• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 387.15157227
• Heavy Atom Count: 26
• Complexity: 575

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC(C(C1)COS(=O)(=O)C)C2=CC=C(C=C2)F
• Isomeric SMILES: CC(C)(C)OC(=O)N1CC[C@H]([C@@H](C1)COS(=O)(=O)C)C2=CC=C(C=C2)F

Technology Process of (3S)-3beta-(Methylsulfonyloxymethyl)-4alpha-(4-fluorophenyl)piperidine-1-carboxylic acid tert-butyl ester

There total 36 articles about (3S)-3beta-(Methylsulfonyloxymethyl)-4alpha-(4-fluorophenyl)piperidine-1-carboxylic acid tert-butyl ester 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:

methanesulfonyl chloride (124-63-0) + (3S,4R)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine-1-carboxylic acid tert-butyl ester (200572-33-4) → (3S,4R)-tert-butyl 4-(4-fluorophenyl)-3-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate (200572-34-5)

Guidance literature:

With triethylamine; In toluene; at 22 - 25 ℃; for 1.25h;

DOI:10.1248/cpb.48.529

Reference yield:

(3S,4R)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine-1-carboxylic acid tert-butyl ester (200572-33-4) + Methanesulfonic anhydride (7143-01-3) → (3S,4R)-tert-butyl 4-(4-fluorophenyl)-3-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate (200572-34-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (3S,4R)-tert-butyl 4-(4-fluorophenyl)-3-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate (200572-34-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 359 mg / aq. sodium hydroxide / tetrahydrofuran / 14 h / 20 °C

2: triethylamine / toluene / 2 h / 23 °C

With sodium hydroxide; triethylamine; In tetrahydrofuran; toluene;

DOI:10.1021/ja037177o

upstream raw materials:

methanesulfonyl chloride

(3S,4R)-4-(4-fluorophenyl)-3-hydroxymethylpiperidine-1-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

4-fluorobenzaldehyde

Downstream raw materials:

(3S,4R)-1-(tert-butoxycarbonyl)-4-(p-fluorophenyl)-3-[3,4-(methylenedioxy)phenoxymethyl]piperidine

tert-butyl (3S,4R)-3-[(1,3-dihydro-2-benzofuran-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine-1-carboxylate

paroxetine

paroxetine