9-Benzyl-1-oxa-9-azaspiro[5.5]undecan-4-yl methanesulfonate

Base Information

• Chemical Name: 9-Benzyl-1-oxa-9-azaspiro[5.5]undecan-4-yl methanesulfonate
• CAS No.: 503551-94-8
• Molecular Formula: C₁₇H₂₅NO₄S
• Molecular Weight: 339.456
• DSSTox Substance ID: DTXSID301149820
• Nikkaji Number: J1.821.266H
• Mol file: 503551-94-8.mol

Synonyms:503551-94-8;9-benzyl-1-oxa-9-azaspiro[5.5]undecan-4-yl methanesulfonate;9-benzyl-1-oxa-9-azaspiro[5.5]undec-4-yl methanesulfonate hydrochloride;starbld0012361;DTXSID301149820;AKOS015959899;CS-0303722;EN300-102875;1-Oxa-9-azaspiro[5.5]undecan-4-ol, 9-(phenylmethyl)-, 4-methanesulfonate

Chemical Property of 9-Benzyl-1-oxa-9-azaspiro[5.5]undecan-4-yl methanesulfonate

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 339.15042945
• Heavy Atom Count: 23
• Complexity: 473

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CS(=O)(=O)OC1CCOC2(C1)CCN(CC2)CC3=CC=CC=C3

Technology Process of 9-Benzyl-1-oxa-9-azaspiro[5.5]undecan-4-yl methanesulfonate

There total 1 articles about 9-Benzyl-1-oxa-9-azaspiro[5.5]undecan-4-yl methanesulfonate 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: 65.0%

1-phenylmethyl-4-piperidone (3612-20-2) + methanesulfonic acid (75-75-2,98527-29-8) + homoalylic alcohol (627-27-0) → methanesulfonic acid 9-benzyl-1-oxa-9-azaspiro[5.5]undec-4-yl ester (503551-94-8)

Guidance literature:

In dichloromethane; at 23 ℃;

DOI:10.3987/com-02-s(m)63

Reference yield:

methanesulfonic acid 9-benzyl-1-oxa-9-azaspiro[5.5]undec-4-yl ester (503551-94-8) → C16H22N4O

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.bioorg.2018.07.014

Reference yield:

methanesulfonic acid 9-benzyl-1-oxa-9-azaspiro[5.5]undec-4-yl ester (503551-94-8) → 9-benzyl-1-oxa-9-azaspiro[5.5]undecan-4-amine

Guidance literature:

Multi-step reaction with 2 steps

1: sodium azide / N,N-dimethyl-formamide / 12 h / 80 °C / Inert atmosphere

2: triphenylphosphine / methanol; water / 3 h / Inert atmosphere; Reflux

With sodium azide; triphenylphosphine; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/j.bioorg.2018.07.014

upstream raw materials:

1-phenylmethyl-4-piperidone

methanesulfonic acid

homoalylic alcohol

Downstream raw materials:

tert-butyl 4-hydroxy-1-oxa-9-azaspiro[5.5]undecane-9-carboxylate

Refernces

• 1、 Lukin, Alexey,Kramer, Jan,Hartmann, Markus,Weizel, Lilia,Hernandez-Olmos, Victor,Falahati, Konstantin,Burghardt, Irene,Kalinchenkova, Natalia,Bagnyukova, Darya,Zhurilo, Nikolay,Rautio, Jarkko,Forsberg, Markus,Ihalainen, Jouni,Auriola, Seppo,Lepp?nen, Jukka,Konstantinov, Igor,Pogoryelov, Denys,Proschak, Ewgenij,Dar'in, Dmitry,Krasavin, Mikhail. "Discovery of polar spirocyclic orally bioavailable urea inhibitors of soluble epoxide hydrolase". . p. 655 - 667. Retrieved 2018/07/31.
• 2、 Ghosh, Arun K.,Shin, Dongwoo,Schiltz, Gary. "Multicomponent reactions: Synthesis of spirocyclic tetrahydropyran derivatives by prins cyclization". . p. 659 - 666. Retrieved 2007/10/03.