1-tert-Butyl 2-methyl 4-oxopiperidine-1,2-dicarboxylate

Base Information

• Chemical Name: 1-tert-Butyl 2-methyl 4-oxopiperidine-1,2-dicarboxylate
• CAS No.: 81357-18-8
• Molecular Formula: C12H19 N O5
• Molecular Weight: 257.287
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID30439324
• Mol file: 81357-18-8.mol

Synonyms:81357-18-8;1-tert-Butyl 2-methyl 4-oxopiperidine-1,2-dicarboxylate;METHYL 1-BOC-4-OXOPIPERIDINE-2-CARBOXYLATE;Methyl N-Boc-4-oxo-piperidine-2-carboxylate;1-BOC-4-OXO-PIPERIDINE-2-CARBOXYLIC ACID METHYL ESTER;1-O-tert-butyl 2-O-methyl 4-oxopiperidine-1,2-dicarboxylate;4-OXO-1,2-PIPERIDINEDICARBOXYLIC ACID 1-(TERT-BUTYL) 2-METHYL ESTER;MFCD09842531;1,2-Piperidinedicarboxylicacid, 4-oxo-, 1-(1,1-dimethylethyl) 2-methyl ester;Levogyration camphorquinone;SCHEMBL4864314;DTXSID30439324;(R)-4-Oxo-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester;(S)-4-Oxo-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester;ROHLQPZIUYTLGR-UHFFFAOYSA-N;AM1193;AKOS015950562;AB53727;CS-W000565;SB34407;SB38604;DS-15775;SY005909;FT-0685081;FT-0720880;J-502378;J-522619;1-tert-Butyl2-methyl4-oxopiperidine-1,2-dicarboxylate;racemic (+/-)-methyl 1-tert-butoxycarbonyl-4-oxopiperidine-2-carboxylate;1,2-Piperidinedicarboxylic acid, 4-oxo-, 1-(1,1-dimethylethyl) 2-methyl ester;4-OXO-PIPERIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER 2-METHYL ESTER

Chemical Property of 1-tert-Butyl 2-methyl 4-oxopiperidine-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.483
• Boiling Point: 350.011 ºC at 760 mmHg
• PKA: -3.59±0.40(Predicted)
• Flash Point: 165.481 ºC
• PSA: 72.91000
• Density: 1.175
• LogP: 1.06590
• Storage Temp.: 2-8°C
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 257.12632271
• Heavy Atom Count: 18
• Complexity: 358

Purity/Quality:

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

Methyl 1-Boc-4-oxopiperidine-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC(=O)CC1C(=O)OC

Technology Process of 1-tert-Butyl 2-methyl 4-oxopiperidine-1,2-dicarboxylate

There total 9 articles about 1-tert-Butyl 2-methyl 4-oxopiperidine-1,2-dicarboxylate 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: 93.0%

4-Oxo-3,4-dihydro-2H-pyridine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester → 4-oxo-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (81357-18-8,1799811-83-8)

Guidance literature:

With hydrogen; catalytic hydrogenation;

DOI:10.1016/S0040-4039(01)82993-2

Reference yield: 92.0%

N-tert-butoxycarbonyl-cis-4-hydroxy-L-pipecolinic acid methyl ester (187753-13-5,181269-87-4) → 4-oxo-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (81357-18-8,1799811-83-8)

Guidance literature:

In dichloromethane; at 20 ℃; for 4h;

Reference yield:

1-benzyl-4-hydroxypiperidine-2-carboxylic acid → 4-oxo-piperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (81357-18-8,1799811-83-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogen / palladium 10% on activated carbon / 24 h / 2585.81 Torr

2.1: triethylamine / 1,4-dioxane; water / 0 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

3.2: 1.5 h / -78 - -40 °C

With oxalyl dichloride; hydrogen; dimethyl sulfoxide; triethylamine; palladium 10% on activated carbon; In 1,4-dioxane; dichloromethane; water;

upstream raw materials:

2-trimethylsilyloxy-1,3-butadiene

[(E)-tert-Butoxycarbonylimino]-acetic acid methyl ester

triphenyl(t-butoxycarbonylimino)phosphorane

N-tert-butoxycarbonyl-cis-4-hydroxy-L-pipecolinic acid methyl ester

Downstream raw materials:

N-Boc-4-hydroxy-4-allylproline methyl ester

methyl 4-oxopiperidine-2-carboxylate

N-tert-butoxycarbonyl-cis-4-hydroxy-L-pipecolinic acid methyl ester

C₁₅H₂₀N₂O₄

Refernces

• 1、 -. "Novel lincomycin derivatives possessing antibacterial activity". . . Retrieved 2008/06/13.
• 2、 -. "AMINO ACID DERIVATIVES". Page column 43-44. . Retrieved 2010/01/30.