(R)-1-((Benzyloxy)carbonyl)piperidine-2-carboxylic acid

Base Information

• Chemical Name: (R)-1-((Benzyloxy)carbonyl)piperidine-2-carboxylic acid
• CAS No.: 28697-09-8
• Molecular Formula: C₁₄H₁₇NO₄
• Molecular Weight: 263.293
• Hs Code.: 2933399090
• European Community (EC) Number: 626-877-5
• DSSTox Substance ID: DTXSID90350884
• Wikidata: Q82126968
• Mol file: 28697-09-8.mol

Synonyms:28697-09-8;(R)-1-((Benzyloxy)carbonyl)piperidine-2-carboxylic acid;(D)-N-(BENZYLOXYCARBONYL)PIPECOLIC ACID;(R)-1-(Benzyloxycarbonyl)-2-piperidinecarboxylic Acid;(D)-N-CBZ-PIPECOLIC ACID;(2R)-1-phenylmethoxycarbonylpiperidine-2-carboxylic acid;(R)-1-CBZ-PIPERIDINE-2-CARBOXYLIC ACID;(2R)-1-[(BENZYLOXY)CARBONYL]PIPERIDINE-2-CARBOXYLIC ACID;z-d-pip-oh;N-Cbz-(R)-(+)-pipecolinic acid;Cbz-D-hPro-OH;1-benzyloxycarbonylpiperidine-2-carboxylic acid;1-CBZ-(R)-PIPERIDINE-2-CARBOXYLIC ACID;(R)-1-Benzyl 1,2-Piperidinedicarboxylate;SCHEMBL82714;(r)-(+)-N-cbz-pipecolic acid;DTXSID90350884;ZSAIHAKADPJIGN-GFCCVEGCSA-N;MFCD01863738;AKOS010366802;AKOS015855922;AS-71483;CS-0199076;EN300-59229;D84606;A819542;(R)-(+)-1-Cbz-2-piperidinecarboxylic acid, 97%;J-017199;(2R)-1-[(benzyloxy)carbonyl]piperidine-2-carboxylate;(R)-1-(benzyloxycarbonyl)piperidine-2-carboxylic acid;N-BENZYLOXYCARBONYL-(R)-(+)-PIPECOLINIC ACID;(R)-1-((Benzyloxy)carbonyl)piperidine-2-carboxylicacid

Chemical Property of (R)-1-((Benzyloxy)carbonyl)piperidine-2-carboxylic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.16E-08mmHg at 25°C
• Melting Point: 111-115 °C(lit.)
• Refractive Index: 1.568
• Boiling Point: 443.9 °C at 760 mmHg
• Flash Point: 222.3 °C
• PSA: 66.84000
• Density: 1.265 g/cm³
• LogP: 2.20020
• Storage Temp.: 00C
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 263.11575802
• Heavy Atom Count: 19
• Complexity: 325

Purity/Quality:

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

(R)-1-(Benzyloxycarbonyl)-2-piperidinecarboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-38-37-36
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(C(C1)C(=O)O)C(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1CCN([C@H](C1)C(=O)O)C(=O)OCC2=CC=CC=C2

Technology Process of (R)-1-((Benzyloxy)carbonyl)piperidine-2-carboxylic acid

There total 31 articles about (R)-1-((Benzyloxy)carbonyl)piperidine-2-carboxylic 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: 97.0%

benzyl chloroformate (501-53-1,94274-21-2) + (R)-(+)-pipecolic acid (1723-00-8,83680-83-5) → (R)-1-((benzyloxy)carbonyl)piperidine-2-carboxylic acid (28697-07-6,28697-09-8,28697-11-2,71170-88-2)

Guidance literature:

With sodium hydroxide; In water; for 1h; Ambient temperature;

Reference yield: 60.0%

(R)-benzyl 2-((S)-1,2-dihydroxyethyl)piperidine-1-carboxylate → (R)-1-((benzyloxy)carbonyl)piperidine-2-carboxylic acid (28697-07-6,28697-09-8,28697-11-2,71170-88-2)

Guidance literature:

With sodium periodate; ruthenium(III) chloride hexahydrate; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 1h;

DOI:10.1016/j.tetasy.2014.08.001

Reference yield: 52.0%

benzyl-(2S)-2-[(1S)-1,2-dihydroxyethyl]piperidine-1-carboxylate → (R)-1-((benzyloxy)carbonyl)piperidine-2-carboxylic acid (28697-07-6,28697-09-8,28697-11-2,71170-88-2)

Guidance literature:

With ruthenium trichloride; sodium periodate; water; In tetrachloromethane; acetonitrile; at 20 ℃; for 2h;

DOI:10.1016/0957-4166(95)00382-7

upstream raw materials:

benzyl chloroformate

(R)-(+)-pipecolic acid

(R)-N-(benzyloxycarbonyl)-2-formylpiperidine

ethyl 5-bromovalerate

Downstream raw materials:

(R)-(+)-pipecolic acid

C₃₇H₅₅N₅O₇S

methyl (2S,4R)-4-[({2-[(1R,3R)-1-acetoxy-4-methyl-3-{[(2S,3S)-3-methyl-2-({[(2R)-1-methylpiperidin-2-yl]carbonyl}amino)pentanoyl]amino}pentyl]-1,3-thiazol-4-yl}carbonyl)amino]-2-methyl-5-phenylpentanoate

(R)-benzyl 2-((2S,3S)-1-((1R,3R)-1-acetoxy-1-(4-((2R,4S)-5-methoxy-4-methyl-5-oxo-1-phenylpentan-2-ylcarbamoyl)thiazol-2-yl)-4-methylpentan-3-ylamino)-3-methyl-1-oxopentan-2-ylcarbamoyl)piperidine-1-carboxylate

Refernces

• 1、 Chavan, Subhash P.,Khairnar, Lalit B.,Chavan, Prakash N.,Kalbhor, Dinesh B.. "A short enantioselective total synthesis of (R)- and (S)-pipecolic acid". . p. 1246 - 1251. Retrieved 2015/02/19.
• 2、 Suzuki,Aoyagi,Kibayashi. "Asymmetric total synthesis of (R)-(-)-cryptopleurine and (R)-(-)-julandine via highly enantioselective amidoalkylations with N-acylhydrazonium salts". . p. 6114 - 6122. Retrieved 2007/10/03.