tert-Butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Base Information

• Chemical Name: tert-Butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate
• CAS No.: 930785-40-3
• Molecular Formula: C13H24N2O3
• Molecular Weight: 256.345
• Hs Code.: 2934999090
• European Community (EC) Number: 801-986-2
• DSSTox Substance ID: DTXSID20693372
• Mol file: 930785-40-3.mol

Synonyms:930785-40-3;tert-Butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate;9-Boc-1-oxa-4,9-diazaspiro[5.5]undecane;MFCD11227065;tert-Butyl 1-oxa-4,9-diazaspiro-[5.5]undecane-9-carboxylate;SCHEMBL996189;DTXSID20693372;FRROFBJYHIEDPS-UHFFFAOYSA-N;TERT-BUTYL1-OXA-4,9-DIAZASPIRO[5.5]UNDECANE-9-CARBOXYLATE;1-oxa-4,9-diaza-spiro[5.5]undecane-9-carboxylic acid tert-butyl ester;AKOS015900842;CS-W005674;PB22496;AC-31611;AM804562;DS-12165;SY096851;FT-0703129;EN300-113744;A850302;J-519494;Z1302367988

Chemical Property of tert-Butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.514
• Boiling Point: 364.211 °C at 760 mmHg
• PKA: 8.82±0.20(Predicted)
• Flash Point: 174.069 °C
• PSA: 50.80000
• Density: 1.113g/cm³
• LogP: 1.64260
• Storage Temp.: 2-8°C
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 256.17869263
• Heavy Atom Count: 18
• Complexity: 304

Purity/Quality:

98%,99%, ^*data from raw suppliers

tert-Butyl1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC2(CC1)CNCCO2

Technology Process of tert-Butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

There total 9 articles about tert-Butyl 1-oxa-4,9-diazaspiro[5.5]undecane-9-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: 95.0%

tert-butyl 3-oxo-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (1160247-07-3) → 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylic acid tert-butyl ester (930785-40-3)

Guidance literature:

tert-butyl 3-oxo-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate; With borane-THF; In tetrahydrofuran; at 55 ℃;

With N,N,N,N,-tetramethylethylenediamine; In methanol; for 6h; Reflux;

DOI:10.1016/j.bmcl.2010.10.016

Reference yield:

4-benzyl 9-tert-butyl 1-oxa-4,9-diazaspiro[5.5]undecane-4,9-dicarboxylate (1097920-69-8) → 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylic acid tert-butyl ester (930785-40-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 50 ℃; for 12h; under 2585.81 Torr; Inert atmosphere;

Reference yield:

4-aminomethyl-4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (392331-66-7) → 1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylic acid tert-butyl ester (930785-40-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium carbonate / water; ethyl acetate / 0.5 h / 0 °C

2.1: potassium tert-butylate / tetrahydrofuran; tert-butyl alcohol / 20 °C / Reflux

3.1: dimethylsulfide borane complex / tetrahydrofuran / 2 h / 55 °C

3.2: Reflux

With dimethylsulfide borane complex; potassium tert-butylate; potassium carbonate; In tetrahydrofuran; water; ethyl acetate; tert-butyl alcohol;

upstream raw materials:

tert-butyl 3-oxo-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

4-aminomethyl-4-hydroxypiperidine-1-carboxylic acid tert-butyl ester

1-oxa-6-aza-spiro-[2.5]octane-6-caboxylic acid tert-butyl ester

N-tert-butyloxycarbonylpiperidin-4-one

Downstream raw materials:

tert-butyl 4-benzyl-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Refernces

• 1、 -. "HETEROCYCLIC SPIRO COMPOUNDS AS MAGL INHIBITORS". Paragraph 0243; 0244; 0246. . Retrieved 2018/08/09.
• 2、 -. "INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL". Page/Page column 49. . Retrieved 2016/05/19.