(S)-1-Boc-2-azetidinemethanol

Base Information

• Chemical Name: (S)-1-Boc-2-azetidinemethanol
• CAS No.: 161511-85-9
• Molecular Formula: C9H17NO3
• Molecular Weight: 187.239
• Hs Code.: 2933990090
• European Community (EC) Number: 840-224-3
• DSSTox Substance ID: DTXSID40441019
• Nikkaji Number: J1.185.464H
• Wikidata: Q72448606
• Mol file: 161511-85-9.mol

Synonyms:(S)-1-Boc-2-azetidinemethanol;161511-85-9;(S)-1-(tert-Butoxycarbonyl)-2-azetidinemethanol;tert-butyl (2S)-2-(hydroxymethyl)azetidine-1-carboxylate;(S)-tert-butyl 2-(hydroxymethyl)azetidine-1-carboxylate;(S)-1-BOC-2-HYDROXYMETHYLAZETIDINE;(S)-2-HYDROXYMETHYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;MFCD03093620;SCHEMBL71903;1-BOC-2-(S)-azetidinemethanol;DTXSID40441019;1-BOC-2-(S)-azetidinylmethanol;XIRUXUKRGUFEKC-ZETCQYMHSA-N;AKOS015838371;CS-W008447;DS-1771;(S)-1-t-butoxycarbonyl-2-azetidinemethanol;1-t-butoxycarbonyl-2-(S)-azetidinemethanol;A3578;AM20080442;B2123;1-t-butyloxycarbonyl-2-(S)-azetidinemethanol;(2S)-1-t-butyloxycarbonyl-2-azetidinemethanol;EN300-298275;N-t-Butoxycarbonyl-2(S)-hydroxymethylazetidine;(S)-1-(tert-butoxycarbonyl)azetidine-2-methanol;(S)-N-tert-butoxycarbonyl-azetidin-2-ylmethanol;1-(tert-butoxycarbonyl)-2(S)-azetidinylmethanol;(2S)-1-(tert-Butoxycarbonyl)azetidine-2-methanol;(S)-N-TERT-BUTOXYCARBONYL-2-HYDROXYMETHYLAZETIDINE;(2S)-2-(hydroxymethyl)-1-azetidinecarboxylic acid tert-butyl ester;2-(S)-Hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester;tert-Butyl (2S)-2-(hydroxymethyl)-1-azetidinecarboxylate, AldrichCPR;1-AZETIDINECARBOXYLIC ACID, 2-(HYDROXYMETHYL)-, 1,1-DIMETHYLETHYL ESTER, (2S)-

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

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: -74 ° (C=1, MeOH)
• 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

(S)-1-(tert-Butoxycarbonyl)-2-azetidinemethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

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: (S)-1-(tert-Butoxycarbonyl)-2-azetidinemethanol is used for synthesis and the study of nicotinic receptor binding of PET ligand [18F]fluoroazetidinylmethoxypyridine.

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

There total 15 articles about (S)-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: 100.0%

(S)-1-(t-butoxycarbonyl)azetidine-2-carboxylic acid (51077-14-6) → 2-(S)-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester (161511-85-9)

Guidance literature:

With borane; In tetrahydrofuran; at 20 ℃; for 48h;

DOI:10.1021/jm0506625

Reference yield: 99.0%

di-tert-butyl dicarbonate (24424-99-5) + (2S)-azetidine-2-carboxylic acid (2133-34-8,20063-89-2) → 2-(S)-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester (161511-85-9)

Guidance literature:

(2S)-azetidine-2-carboxylic acid; With borane-THF; In tetrahydrofuran; for 1.25h; Heating;

With potassium hydrogensulfate; In tetrahydrofuran; water; for 0.25h; Heating;

di-tert-butyl dicarbonate; With sodium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 3h;

DOI:10.1002/jlcr.569

Reference yield: 97.0%

di-tert-butyl dicarbonate (24424-99-5) + tert-butylmagnesium chloride (677-22-5) + (S)-4-isopropoxycarbonyl-2-azetidinone (155878-39-0) + (S)-azetidine-2-methanol (104587-62-4,250274-91-0) → 2-(S)-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester (161511-85-9)

Guidance literature:

With sodium bicarbonate; sulfuric acid; magnesium chloride; In tetrahydrofuran; water; ethyl acetate; toluene;

upstream raw materials:

(S)-1-(t-butoxycarbonyl)azetidine-2-carboxylic acid

methyl N-tert-butyloxycarbonyl-L-azetidine-2-carboxylate

(S)-1-(t-butoxycarbonyl)-2-{[(t-butyldimethyl)silyloxy]methyl}azetidine

di-tert-butyl dicarbonate

Downstream raw materials:

tert-butyl (S)-2-(phenoxymethyl)azetidine-1-carboxylate

C₁₉H₂₅N₃O₄

C₁₉H₂₄FN₃O₄

C₂₀H₂₅N₃O₆

Refernces

• 1、 Dollé, Frédéric,Dolci, Lilian,Valette, Héric,Hinnen, Fran?oise,Vaufrey, Fran?oise,Guenther, Ilonka,Fuseau, Chantal,Coulon, Christine,Bottlaender, Michel,Crouzel, Christian. "Synthesis and nicotinic acetylcholine receptor in vivo binding properties of 2-fluoro-3-[2(S)-2-azetidinylmethoxy]pyridine: A new positron emission tomography ligand for nicotinic receptors". . p. 2251 - 2259. Retrieved 1999.
• 2、 Kimura, Hiroyuki,Ueda, Masashi,Kawashima, Hidekazu,Arimitsu, Kenji,Yagi, Yusuke,Saji, Hideo. "Synthesis and biological evaluation of Tc-99m-cyclopentadienyltricarbonyl-technetium-labeled A-85380: An imaging probe for single-photon emission computed tomography investigation of nicotinic acetylcholine receptors in the brain". . p. 2245 - 2252. Retrieved 2019/04/30.
• 3、 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.