(R)-1-Boc-2-azetidinemethanol

Base Information

• Chemical Name: (R)-1-Boc-2-azetidinemethanol
• CAS No.: 161511-90-6
• Molecular Formula: C9H17NO3
• Molecular Weight: 187.239
• Hs Code.: 2933998090
• DSSTox Substance ID: DTXSID20454228
• Nikkaji Number: J995.455D
• Wikidata: Q72448609
• Mol file: 161511-90-6.mol

Synonyms:(R)-1-Boc-2-azetidinemethanol;161511-90-6;(R)-1-(tert-Butoxycarbonyl)-2-azetidinemethanol;Tert-butyl (2R)-2-(hydroxymethyl)azetidine-1-carboxylate;(R)-tert-butyl 2-(hydroxymethyl)azetidine-1-carboxylate;(R)-2-HYDROXYMETHYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;MFCD03790937;(S)-tert-butyl 2-(hydroxymethyl)azetidine-1-carboxylate;SCHEMBL283443;1-BOC-2-(R)-azetidinemethanol;DTXSID20454228;XIRUXUKRGUFEKC-SSDOTTSWSA-N;AKOS015841262;AKOS015901313;CS-W016849;(2R)-1-Boc-2-(hydroxymethyl)azetidine;AC-26595;AS-42703;(R)-1-t-butoxycarbonyl-2-azetidinemethanol;A3579;AM20080443;B2174;(R)-1-t-butyloxycarbonyl-2-azetidinemethanol;EN300-658360;1-(tert-butoxycarbonyl)-2(R)-azetidinylmethanol;1-t-butoxycarbonyl-2-(R)-hydroxymethyiazetidine;1-t-butoxycarbonyl-2-(R)-hydroxymethylazetidine;1-(tert-butoxycarbonyl)-2-(R)-azetidinylmethanol;(2R)-1-(tert-Butyloxycarbonyl)azetidine-2-methanol;[1-(tert-Butoxycarbonyl)-2(R)-azetidinyl]methanol;J-009834;J-502532;tert-butyl (R)-2-hydroxymethylazetidine-1-carboxylate;(R)-2-(Hydroxymethyl)-1-azetidinecarboxylic acid tert-butyl ester;1-Azetidinecarboxylic acid, 2-(hydroxymethyl)-, 1,1-dimethylethyl ester, (2R)-

Chemical Property of (R)-1-Boc-2-azetidinemethanol

Chemical Property:

• Refractive Index: 1.4580-1.4620
• Boiling Point: 270.349 °C at 760 mmHg
• PKA: 14.77±0.10(Predicted)
• Flash Point: 117.303 °C
• PSA: 49.77000
• Density: 1.116 g/cm³
• LogP: 0.92600
• Storage Temp.: 2-8°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 187.12084340
• Heavy Atom Count: 13
• Complexity: 198

Purity/Quality:

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

(2R)-1-Boc-2-(hydroxymethyl)azetidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC1CO
• Isomeric SMILES: CC(C)(C)OC(=O)N1CC[C@@H]1CO
• Uses: (2R)-1-Boc-2-(hydroxymethyl)azetidine was used to study analgesic structure activity relationship of (azetidinylmethoxy)chloropyridine derivatives. It is used for efficient asymmetric synthesis of oral analgesic.

Technology Process of (R)-1-Boc-2-azetidinemethanol

There total 6 articles about (R)-1-Boc-2-azetidinemethanol 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%

(R)-N-(tert-butoxycarbonyl)azetidine-2-carboxylic acid (228857-58-7) → (R)-1-t-butyloxycarbonyl-2-azetidinemethanol (161511-90-6)

Guidance literature:

(R)-N-(tert-butoxycarbonyl)azetidine-2-carboxylic acid; With sodium tetrahydroborate; In Isopropyl acetate; at 0 - 20 ℃; for 0.25h;

With boron trifluoride diethyl etherate; In Isopropyl acetate; at 0 - 10 ℃; for 4h;

DOI:10.1021/acs.joc.6b00149

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + benzyl (2R)-4-oxoazetidine-2-carboxylate (95729-87-6) → (R)-1-t-butyloxycarbonyl-2-azetidinemethanol (161511-90-6)

Guidance literature:

With sodium hydroxide; LiAlH₄; In tetrahydrofuran; water;

Reference yield:

C14H23NO6 → (R)-1-t-butyloxycarbonyl-2-azetidinemethanol (161511-90-6)

Guidance literature:

With sodium tetrahydroborate; In water; at 0 - 20 ℃;

DOI:10.1021/acs.jmedchem.6b01559

upstream raw materials:

(R)-N-(tert-butoxycarbonyl)azetidine-2-carboxylic acid

di-tert-butyl dicarbonate

(2R)-2-azetidinylmethanol

benzyl (2R)-4-oxoazetidine-2-carboxylate

Downstream raw materials:

(R)-tert-butyl 2-((5-bromopyridin-3-yloxy)methyl)azetidine-1-carboxylate

(R)-azetidin-2-ylmethanol hydrochloride

(R)-tert-butyl 2-(aminomethyl)azetidine-1-carboxylate

(R)-tert-butyl 2-((5-(phenylethynyl)pyridin-3-yloxy)methyl)azetidine-1-carboxylate

Refernces

• 1、 Angst, Daniela,Gessier, Fran?ois,Janser, Philipp,Vulpetti, Anna,W?lchli, Rudolf,Beerli, Christian,Littlewood-Evans, Amanda,Dawson, Janet,Nuesslein-Hildesheim, Barbara,Wieczorek, Grazyna,Gutmann, Sascha,Scheufler, Clemens,Hinniger, Alexandra,Zimmerlin, Alfred,Funhoff, Enrico G.,Pulz, Robert,Cenni, Bruno. "Discovery of LOU064 (Remibrutinib), a Potent and Highly Selective Covalent Inhibitor of Bruton's Tyrosine Kinase". supporting information. p. 5102 - 5118. Retrieved 2020/06/10.
• 2、 Jurica, Elizabeth A.,Wu, Ximao,Williams, Kristin N.,Hernandez, Andres S.,Nirschl, David S.,Rampulla, Richard A.,Mathur, Arvind,Zhou, Min,Cao, Gary,Xie, Chunshan,Jacob, Biji,Cai, Hong,Wang, Tao,Murphy, Brian J.,Liu, Heng,Xu, Carrie,Kunselman, Lori K.,Hicks, Michael B.,Sun, Qin,Schnur, Dora M.,Sitkoff, Doree F.,Dierks, Elizabeth A.,Apedo, Atsu,Moore, Douglas B.,Foster, Kimberly A.,Cvijic, Mary Ellen,Panemangalore, Reshma,Flynn, Neil A.,Maxwell, Brad D.,Hong, Yang,Tian, Yuan,Wilkes, Jason J.,Zinker, Bradley A.,Whaley, Jean M.,Barrish, Joel C.,Robl, Jeffrey A.,Ewing, William R.,Ellsworth, Bruce A.. "Discovery of Pyrrolidine-Containing GPR40 Agonists: Stereochemistry Effects a Change in Binding Mode". . p. 1417 - 1431. Retrieved 2017/03/08.