(3S,4S)-tert-butyl 4-(benzylamino)-3-fluoropiperidine-1-carboxylate

Base Information

• Chemical Name: (3S,4S)-tert-butyl 4-(benzylamino)-3-fluoropiperidine-1-carboxylate
• CAS No.: 211108-52-0
• Molecular Formula: C17H25FN2O2
• Molecular Weight: 308.39100
• Hs Code.: 2933399990
• DSSTox Substance ID: DTXSID601126742
• Mol file: 211108-52-0.mol

Synonyms:SCHEMBL2292403;JXBLMDWEOQDVAC-GJZGRUSLSA-N;DTXSID601126742;(3S,4S) tert-butyl 4-(benzyl amino)-3-fluoropiperidine-1-carboxylate;(3S,4S)-tert-butyl 4-(benzylamino)-3-fluoropiperidine-1-carboxylate;rel-1,1-Dimethylethyl (3R,4R)-3-fluoro-4-[(phenylmethyl)amino]-1-piperidinecarboxylate

Chemical Property of (3S,4S)-tert-butyl 4-(benzylamino)-3-fluoropiperidine-1-carboxylate

Chemical Property:

• Boiling Point: 405.0±45.0 °C(Predicted)
• PKA: 7.98±0.40(Predicted)
• PSA: 41.57000
• Density: 1.11±0.1 g/cm3(Predicted)
• LogP: 3.45250
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 308.19000621
• Heavy Atom Count: 22
• Complexity: 364

Purity/Quality:

NLT 98% ^*data from raw suppliers

tert-Butyl 3,4-trans-4-(benzylamino)-3-fluoropiperidine-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC(C(C1)F)NCC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N1CC[C@@H]([C@H](C1)F)NCC2=CC=CC=C2

Technology Process of (3S,4S)-tert-butyl 4-(benzylamino)-3-fluoropiperidine-1-carboxylate

There total 67 articles about (3S,4S)-tert-butyl 4-(benzylamino)-3-fluoropiperidine-1-carboxylate 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: 63.0%

benzylamine (100-46-9) + tert-butyl-3-fluoro-4-oxopiperidine-1-carboxylate (211108-50-8) → (±)-cis-4-benzylamino-3-fluoropiperidine-1-carboxylic acid tert-butyl ester (211108-52-0,211108-53-1) + trans-4-benzylamino-1-tert-butoxycarbonyl-3-fluoropiperidine (211108-52-0,211108-53-1)

Guidance literature:

With NaB(OAc)2H; In 1,2-dichloro-ethane; for 2.25h; Ambient temperature;

DOI:10.1021/jm981133m

Reference yield: 63.0%

benzylamine (100-46-9) + tert-butyl-3-fluoro-4-oxopiperidine-1-carboxylate (211108-50-8) → (±)-cis-4-benzylamino-3-fluoropiperidine-1-carboxylic acid tert-butyl ester (211108-52-0,211108-53-1) + trans-4-benzylamino-1-tert-butoxycarbonyl-3-fluoropiperidine (211108-52-0,211108-53-1)

Guidance literature:

With NaB(OAc)2H; In 1,2-dichloro-ethane; for 2.25h; Ambient temperature;

DOI:10.1021/jm981133m

Reference yield: 60.0%

benzylamine (100-46-9) + tert-butyl-3-fluoro-4-oxopiperidine-1-carboxylate (211108-50-8) → (±)-cis-4-benzylamino-3-fluoropiperidine-1-carboxylic acid tert-butyl ester (211108-52-0,211108-53-1)

Guidance literature:

benzylamine; tert-butyl-3-fluoro-4-oxopiperidine-1-carboxylate; With sodium tris(acetoxy)borohydride; In dichloromethane; at 0 - 20 ℃; for 0.5h; Molecular sieve;

With water; sodium hydrogencarbonate; In dichloromethane;

upstream raw materials:

benzylamine

tert-butyl-3-fluoro-4-oxopiperidine-1-carboxylate

N-tert-butyloxycarbonylpiperidin-4-one

tert-butyl 4-[(trimethylsilyl)oxy]-3,6-dihydropyridine-1(2H)-carboxylate

Downstream raw materials:

(3R,4R)-tert-butyl 4-(benzylamino)-3-fluoropiperidine-1-carboxylate

(3S,4S)-tert-butyl 4-(benzylamino)-3-fluoropiperidine-1-carboxylate

(3R,4R)-tert-butyl 4-amino-3-fluoropiperidine-1-carboxylate

(3S,4S)-tert-butyl 4-amino-3-fluoropiperidine-1-carboxylate

Refernces

• 1、 Benson, Helen,Bones, Karen,Churchill, Gwydion,Ford, Gair,Frodsham, Lianne,Janbon, Sophie,Millington, Fiona,Powell, Lyn,Raw, Steven A.,Reid, Julie,Stark, Andrew,Steven, Alan. "Development of the Convergent, Kilogram-Scale Synthesis of an Antibacterial Clinical Candidate Using Enantioselective Hydrogenation". . p. 588 - 598. Retrieved 2020/05/19.
• 2、 -. "PYRIDINE AND PYRAZINE COMPOUNDS AS INHIBITORS OF RIPK2". Paragraph 0289; 290. . Retrieved 2018/05/03.