(S)-1-tert-Butyl 2-ethyl 4-oxopiperidine-1,2-dicarboxylate

Base Information

• Chemical Name: (S)-1-tert-Butyl 2-ethyl 4-oxopiperidine-1,2-dicarboxylate
• CAS No.: 180854-44-8
• Molecular Formula: C₁₃H₂₁NO₅
• Molecular Weight: 271.313
• Hs Code.: 2933399990
• European Community (EC) Number: 695-467-6
• Nikkaji Number: J1.515.077G
• Wikidata: Q76417004
• Mol file: 180854-44-8.mol

Synonyms:180854-44-8;Ethyl (S)-1-Boc-4-oxopiperidine-2-carboxylate;(S)-1-tert-Butyl 2-ethyl 4-oxopiperidine-1,2-dicarboxylate;1-tert-butyl 2-ethyl (2S)-4-oxopiperidine-1,2-dicarboxylate;1,2-Piperidinedicarboxylic acid, 4-oxo-, 1-(1,1-dimethylethyl) 2-ethyl ester, (2S)-;1-O-tert-butyl 2-O-ethyl (2S)-4-oxopiperidine-1,2-dicarboxylate;MFCD15071881;AKOS025290208;DS-8025;CS-0052402;P11772;(2S)-Ethyl 1-boc-4-oxopiperidine-2-carboxylate;A881062;Ethyl (S)-(-)-1-Boc-4-oxopiperidine-2-carboxylate;Ethyl (S)-1-Boc-4-oxopiperidine-2-carboxylate, 97%;(S)-1-tert-Butyl2-ethyl4-oxopiperidine-1,2-dicarboxylate;(S)-(-)-1-Boc-4-oxopiperidine-2-carboxylic acid ethyl ester

Chemical Property of (S)-1-tert-Butyl 2-ethyl 4-oxopiperidine-1,2-dicarboxylate

Chemical Property:

• Refractive Index: 1.4600
• Flash Point: >110°(230°F)
• PSA: 72.91000
• Density: 1.079 g/mL at 25 °C
• LogP: 1.45600
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 271.14197277
• Heavy Atom Count: 19
• Complexity: 372

Purity/Quality:

98% ^*data from raw suppliers

(S)-1-Boc-4-oxopiperidine-2-carboxylic acid, methyl ester ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CC(=O)CCN1C(=O)OC(C)(C)C
• Isomeric SMILES: CCOC(=O)[C@@H]1CC(=O)CCN1C(=O)OC(C)(C)C
• Uses: 1-Boc-4-oxopiperidine-2-carboxylate participates in the one-pot in situ formation and reaction of trimethyl (trichloromethyl) silane which finds application in the synthesis of 2, 2, 2-trichloromethylcarbinols.

Technology Process of (S)-1-tert-Butyl 2-ethyl 4-oxopiperidine-1,2-dicarboxylate

There total 6 articles about (S)-1-tert-Butyl 2-ethyl 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: 86.0%

di-tert-butyl dicarbonate (24424-99-5) + (2S)-4-oxopiperidine-2-carboxylic acid ethyl ester (180675-07-4,51339-61-8) → (2S)-N-tert-butoxycarbonyl-4-oxopiperidine-2-carboxylic acid ethyl ester (180854-44-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In ethanol; dichloromethane; at 20 ℃; for 72h;

DOI:10.1016/S0040-4020(01)00429-X

Reference yield:

(1'R)-2-[1'-phenylethyl]-5-(2-hydroxyethyl)isoxazolidine-3-carboxylic acid ethyl ester (357154-22-4) → (2S)-N-tert-butoxycarbonyl-4-oxopiperidine-2-carboxylic acid ethyl ester (180854-44-8)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 4 h / 0 °C

2: 3.29 g / DABCO / acetonitrile / 1 h / 75 °C

3: 94 percent / H₂ / Pd(OH)2/C / ethanol / 24 h / 20 °C / 760 Torr

4: 86 percent / i-Pr₂NEt / CH₂Cl₂; ethanol / 72 h / 20 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; hydrogen; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In ethanol; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(01)00429-X

Reference yield:

(1'R,2S)-4-oxo-1-(1'-phenylethyl)-piperidine-2-carboxylic acid ethyl ester (357154-19-9) → (2S)-N-tert-butoxycarbonyl-4-oxopiperidine-2-carboxylic acid ethyl ester (180854-44-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / H₂ / Pd(OH)2/C / ethanol / 24 h / 20 °C / 760 Torr

2: 86 percent / i-Pr₂NEt / CH₂Cl₂; ethanol / 72 h / 20 °C

With hydrogen; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In ethanol; dichloromethane;

DOI:10.1016/S0040-4020(01)00429-X

upstream raw materials:

di-tert-butyl dicarbonate

(2S)-4-oxopiperidine-2-carboxylic acid ethyl ester

(1'R)-2-[1'-phenylethyl]-5-(2-hydroxyethyl)isoxazolidine-3-carboxylic acid ethyl ester

(1'R,2S)-4-oxo-1-(1'-phenylethyl)-piperidine-2-carboxylic acid ethyl ester

Downstream raw materials:

ethyl cis-4-hydroxy-N-t-butoxycarbonyl-2-piperidinecarboxylate

Refernces

• 1、 Machetti, Fabrizio,Cordero, Franca M.,De Sarlo, Francesco,Guarna, Antonio,Brandi, Alberto. "A new synthesis of (2S)-4-oxopipecolic acid by thermal rearrangement of enantiopure spirocyclopropaneisoxazolidine". . p. 4205 - 4208. Retrieved 2007/10/03.