(R)-Benzyl 3-hydroxypiperidine-1-carboxylate

Base Information

• Chemical Name: (R)-Benzyl 3-hydroxypiperidine-1-carboxylate
• CAS No.: 100858-34-2
• Molecular Formula: C13H17NO3
• Molecular Weight: 235.283
• European Community (EC) Number: 848-220-3
• DSSTox Substance ID: DTXSID60426141
• Nikkaji Number: J1.192.572C
• Wikidata: Q82239109
• Mol file: 100858-34-2.mol

Synonyms:100858-34-2;(R)-Benzyl 3-hydroxypiperidine-1-carboxylate;benzyl (3R)-3-hydroxypiperidine-1-carboxylate;(R)-1-Cbz-3-hydroxy-piperidine;R-1-CBZ-3-Hydroxy-piperidine;(R)-Benzyl3-hydroxypiperidine-1-carboxylate;SCHEMBL6128832;DTXSID60426141;1-Piperidinecarboxylic acid, 3-hydroxy-, phenylmethyl ester, (3R)-;AB6218;MFCD11112280;AKOS015855504;AKOS015923359;AC-29689;DS-17807;CS-0038764;EN300-314157;(3R)-3alpha-Hydroxypiperidine-1-carboxylic acid benzyl ester

Chemical Property of (R)-Benzyl 3-hydroxypiperidine-1-carboxylate

Chemical Property:

• Boiling Point: 384.9±42.0 °C(Predicted)
• PKA: 14.72±0.20(Predicted)
• PSA: 49.77000
• Density: 1.220±0.06 g/cm3(Predicted)
• LogP: 1.71780
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 235.12084340
• Heavy Atom Count: 17
• Complexity: 251

Purity/Quality:

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

(R)-1-Cbz-3-hydroxy-piperidine 97.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(CN(C1)C(=O)OCC2=CC=CC=C2)O
• Isomeric SMILES: C1C[C@H](CN(C1)C(=O)OCC2=CC=CC=C2)O

Technology Process of (R)-Benzyl 3-hydroxypiperidine-1-carboxylate

There total 13 articles about (R)-Benzyl 3-hydroxypiperidine-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: 91.0%

N-(benzyloxycarbonyl)-3-piperidone (61995-20-8) → benzyl (3R)-3-hydroxypiperidine-1-carboxylate (100858-34-2)

Guidance literature:

With recombinant Chryseobacterium sp. CA 49 ketoreductase; nicotinamide adenine dinucleotide; In aq. phosphate buffer; isopropyl alcohol; at 40 ℃; for 10h; pH=7.0; stereoselective reaction; Enzymatic reaction;

DOI:10.1016/j.procbio.2017.03.002

Reference yield: 85.4%

(3R)-piperidin-3-ol (62414-68-0) + benzyl chloroformate (501-53-1,94274-21-2) → benzyl (3R)-3-hydroxypiperidine-1-carboxylate (100858-34-2)

Guidance literature:

With sodium hydroxide; sodium hydrogencarbonate; In water; toluene; Ambient temperature;

DOI:10.1016/0040-4020(95)00285-G

Reference yield: 50.0%

benzyl 3-acetoxypiperidine-1-carboxyate (174621-92-2) → benzyl (3R)-3-hydroxypiperidine-1-carboxylate (100858-34-2)

Guidance literature:

With phosphate buffer; In 1,4-dioxane; at 25 ℃; for 90h; lipase PS;

DOI:10.1246/bcsj.69.207

upstream raw materials:

1-benzyloxycarbonyl-1,2,3,6-tetrahydropyridine

(3R)-piperidin-3-ol

benzyl chloroformate

benzyl 3-acetoxypiperidine-1-carboxyate

Downstream raw materials:

(3R)-(aminooxy)-1-(carbobenzyloxy)piperidine

Refernces

• 1、 -. "Preparation methods and applications of chiral spirophosphine-nitrogen-phosphine tridentate ligand and iridium catalyst thereof". Paragraph 0265-0273. . Retrieved 2020/08/18.
• 2、 Kubota, Koji,Watanabe, Yuta,Hayama, Keiichi,Ito, Hajime. "Enantioselective Synthesis of Chiral Piperidines via the Stepwise Dearomatization/Borylation of Pyridines". . p. 4338 - 4341. Retrieved 2016/05/09.