Tert-butyl 2-acetylpiperidine-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 2-acetylpiperidine-1-carboxylate
• CAS No.: 201991-24-4
• Molecular Formula: C₁₂H₂₁NO₃
• Molecular Weight: 227.304
• Hs Code.: 2933399090
• European Community (EC) Number: 875-152-1
• DSSTox Substance ID: DTXSID80472887
• Nikkaji Number: J1.159.800E
• Mol file: 201991-24-4.mol

Synonyms:Tert-butyl 2-acetylpiperidine-1-carboxylate;201991-24-4;2-Acetyl-N-Boc-piperidine;2-ACETYL-1-PIPERIDINECARBOXYLIC ACID TERT-BUTYL ESTER;1-Piperidinecarboxylic acid, 2-acetyl-, 1,1-dimethylethyl ester;MFCD09953375;1-Boc-2-acetyl-piperidine;tert-Butyl2-acetylpiperidine-1-carboxylate;SCHEMBL13804123;1-(1-Boc-2-piperidyl)ethanone;DTXSID80472887;BIA99124;AKOS004910665;SB35172;SB43850;SB47421;AS-42892;SY193192;AM20120460;CS-0005448;EN300-99445;tert-butyl 2-ethanoylpiperidine-1-carboxylate;A814325;Z1330824569

Chemical Property of Tert-butyl 2-acetylpiperidine-1-carboxylate

Chemical Property:

• Boiling Point: 312.365 °C at 760 mmHg
• PKA: -3.16±0.40(Predicted)
• Flash Point: 142.714 °C
• PSA: 46.61000
• Density: 1.053 g/cm³
• LogP: 2.30290
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 227.15214353
• Heavy Atom Count: 16
• Complexity: 281

Purity/Quality:

98% or more ^*data from raw suppliers

tert-Butyl2-Acetylpiperidine-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1CCCCN1C(=O)OC(C)(C)C

Technology Process of Tert-butyl 2-acetylpiperidine-1-carboxylate

There total 6 articles about Tert-butyl 2-acetylpiperidine-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: 97.0%

methylmagnesium bromide (75-16-1) + 2-(methoxy-N-methylcarbamoyl)piperidine-1-carboxylic acid tert-butyl ester (211310-10-0) → 1-tert-butoxycarbonyl-2-acetylpiperidine (201991-24-4,1260601-32-8)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 2h;

Reference yield:

1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid (98303-20-9) → 1-tert-butoxycarbonyl-2-acetylpiperidine (201991-24-4,1260601-32-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / Ph₃P / acetonitrile / Heating

2: diethyl ether

With triphenylphosphine; In diethyl ether; acetonitrile;

DOI:10.1021/jf9706437

Reference yield:

pipecolic Acid (4043-87-2,83680-83-5) → 1-tert-butoxycarbonyl-2-acetylpiperidine (201991-24-4,1260601-32-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / Et₃N / dioxane; H₂O / 2 h / Ambient temperature

2: 87 percent / Ph₃P / acetonitrile / Heating

3: diethyl ether

With triethylamine; triphenylphosphine; In 1,4-dioxane; diethyl ether; water; acetonitrile;

DOI:10.1021/jf9706437

upstream raw materials:

methylmagnesium bromide

2-(Pyridin-2-ylsulfanylcarbonyl)-piperidine-1-carboxylic acid tert-butyl ester

2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile

1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid

Downstream raw materials:

2-[2-(2-aminophenyl)-1-methylvinyl]piperidine-1-carboxylic acid tert-butyl ester

(Z)-1-Boc-2-(1-(2-azidophenyl)prop-1-en-2-yl)piperidine

(Z)-2-(1-(2-azidophenyl)prop-1-en-2-yl)-1-(phenylsulfonyl)piperidine

tert-butyl (6-oxoheptyl)carbamate

Refernces

• 1、 Kong, Chen,Jana, Navendu,Driver, Tom G.. "Rh2(II)-catalyzed selective aminomethylene migration from styryl azides". . p. 824 - 827. Retrieved 2013/03/29.
• 2、 Hofmann, Thomas,Schieberle, Peter. "New and Convenient Syntheses of the Important Roasty, Popcorn-like Smelling Food Aroma Compounds 2-Acetyl-1-pyrroline and 2-Acetyltetrahydropyridine from Their Corresponding Cyclic α-Amino Acids". . p. 616 - 619. Retrieved 2007/10/03.