(R)-2-[(N-benzyloxycarbonyl)piperidin-2-yl]ethanoic acid

Base Information

• Chemical Name: (R)-2-[(N-benzyloxycarbonyl)piperidin-2-yl]ethanoic acid
• CAS No.: 1036403-99-2
• Molecular Formula: C₁₅H₁₉NO₄
• Molecular Weight: 277.32
• Mol file: 1036403-99-2.mol

Synonyms:(R)-2-[(N-benzyloxycarbonyl)piperidin-2-yl]ethanoic acid

Chemical Property of (R)-2-[(N-benzyloxycarbonyl)piperidin-2-yl]ethanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(N-benzyloxycarbonyl)piperidin-2-yl]ethanoic acid

There total 14 articles about (R)-2-[(N-benzyloxycarbonyl)piperidin-2-yl]ethanoic acid 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: 80.0%

benzyl chloroformate (501-53-1,94274-21-2) + (R)-2-(piperidin-2'-yl)ethanoic acid (19832-04-3,55049-18-8,64625-19-0,69222-96-4) → (R)-2-[(N-benzyloxycarbonyl)piperidin-2-yl]ethanoic acid (1036403-99-2,137428-09-2)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 18.33h;

DOI:10.1021/jo101776y

Reference yield: 76.0%

(R)-1-(benzyloxycarbonyl)-2-(2-oxoethyl)piperidine (143264-57-7) → (R)-2-[(N-benzyloxycarbonyl)piperidin-2-yl]ethanoic acid (1036403-99-2,137428-09-2)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20 ℃; for 1h;

DOI:10.1021/jo800749t

Reference yield:

(1R,5S,6S)-N-benzyloxycarbonyl-6-tropanol (1369774-31-1) → (R)-2-[(N-benzyloxycarbonyl)piperidin-2-yl]ethanoic acid (1036403-99-2,137428-09-2)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hypochlorite; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hydrogencarbonate; potassium bromide / water; acetone / 2.08 h / Cooling with ice

2: disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 20 °C

3: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 16 h / -78 °C

With triethylsilane; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; disodium hydrogenphosphate; boron trifluoride diethyl etherate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; potassium bromide; In dichloromethane; water; acetone; 2: Bayer-Villiger oxidation;

DOI:10.1039/c2ob06984a

upstream raw materials:

(3(2(2R)),4S,5R)-3-[2-((N-benzyloxycarbonyl)piperidin-2-yl)-1-oxoethyl]-4-methyl-5-phenyl-2-oxazolidinone

2-[(N-benzyloxycarbonyl)piperidin-2-yl]ethanoic acid

(R)-1-(benzyloxycarbonyl)-2-(2-oxoethyl)piperidine

benzyl chloroformate

Downstream raw materials:

benzyl (2R)-2-(2-(methoxy(methyl)amino)-2-oxoethyl)piperidine-1-carboxylate

(+)-(2R)-(2-oxopropyl)piperidine-1-carbamic acid benzyl ester

(-)-pelletierine

(R)-2-(piperidin-2'-yl)ethanoic acid

Refernces

• 1、 Chiou, Wen-Hua,Chen, Guei-Tang,Kao, Chien-Lun,Gao, Yu-Kai. "Syntheses of (-)-pelletierine and (-)-homopipecolic acid". . p. 2518 - 2520. Retrieved 2012/04/23.
• 2、 Carlson, Erik C.,Rathbone, Lauren K.,Yang, Hua,Collett, Nathan D.,Carter, Rich G.. "Improved protocol for asymmetric, intramolecular heteroatom Michael addition using organocatalysis: Enantioselective syntheses of homoproline, pelletierine, and homopipecolic acid". . p. 5155 - 5158. Retrieved 2008/09/21.