tert-Butyl 2-(hydroxymethyl)azetidine-1-carboxylate

Base Information

• Chemical Name: tert-Butyl 2-(hydroxymethyl)azetidine-1-carboxylate
• CAS No.: 174346-82-8
• Molecular Formula: C9H17NO3
• Molecular Weight: 187.239
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID80564418
• Mol file: 174346-82-8.mol

Synonyms:174346-82-8;1-Boc-2-azetidinemethanol;tert-Butyl 2-(hydroxymethyl)azetidine-1-carboxylate;2-HYDROXYMETHYL-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;1-Azetidinecarboxylic acid, 2-(hydroxymethyl)-, 1,1-dimethylethyl ester;MFCD03790936;MFCD03093620;ALLEOSIDEA;(S)-tert-butyl 2-(hydroxymethyl)azetidine-1-carboxylate;SCHEMBL71904;AMY4282;DTXSID80564418;(S)-1-Boc-azetidine-2-methanol;1-Boc-2-(hydroxymethyl)azetidine;XIRUXUKRGUFEKC-UHFFFAOYSA-N;1-Boc-2-(hyxdroxymethyl)azetidine;ZGA34682;AKOS005264547;PB10267;PB18632;PB20800;AS-42891;SY042243;SY096949;SY097028;CS-0048457;A21782;EN300-154300;tert-Butyl2-(hydroxymethyl)azetidine-1-carboxylate;(+/-)tert-Butyl 2-hydroxymethylazetidine-1-carboxylate;tert-butyl (R)-2-(hydroxymethyl)azetidine-1-carboxylate

Chemical Property of tert-Butyl 2-(hydroxymethyl)azetidine-1-carboxylate

Chemical Property:

• Melting Point: 132-135
• Boiling Point: 270.349 °C at 760 mmHg
• Flash Point: 117.303 °C
• PSA: 49.77000
• Density: 1.116g/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

[1-(tert-Butoxycarbonyl)azetidin-2-yl]methanol ^*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
• Uses: [1-(tert-Butoxycarbonyl)azetidin-2-yl]methanol is used as a potential positiron emission tomography imaging agents for nicotinic acetylcholine receptors.

Technology Process of tert-Butyl 2-(hydroxymethyl)azetidine-1-carboxylate

There total 4 articles about tert-Butyl 2-(hydroxymethyl)azetidine-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: 98.0%

1-(tert-butoxycarbonyl)azetidine-2-carboxylic acid (159749-28-7) → R,S-1-[(1,1-Dimethylethoxy)carbonyl]azetidine-2-methanol (174346-82-8)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 25 ℃; for 3h;

Reference yield:

(1-benzyl-azetidin-2-yl)-methanol (31247-34-4,477585-69-6) + di-tert-butyl dicarbonate (24424-99-5) → R,S-1-[(1,1-Dimethylethoxy)carbonyl]azetidine-2-methanol (174346-82-8)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol;

DOI:10.1021/jm701265n

Reference yield:

azetidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (255882-72-5) → R,S-1-[(1,1-Dimethylethoxy)carbonyl]azetidine-2-methanol (174346-82-8)

Guidance literature:

azetidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester; With sodium tetrahydroborate; In tetrahydrofuran; Heating / reflux;

With methanol; In tetrahydrofuran; for 1.5h; Heating / reflux;

upstream raw materials:

azetidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

(1-benzyl-azetidin-2-yl)-methanol

di-tert-butyl dicarbonate

1-(tert-butoxycarbonyl)azetidine-2-carboxylic acid

Downstream raw materials:

tert-butyl 2-[[4-amino-3-(2-fluoro-4-phenoxy-phenyl)pyrazolo[3,4-d]pyrimidin-1-yl]methyl]azetidine-1-carboxylate

Refernces

• 1、 -. "QUINAZOLINE DERIVATIVES, COMPOSITIONS THEREOF, AND USE AS PHARMACEUTICALS". Page/Page column 38. . Retrieved 2015/02/02.
• 2、 -. "AZETIDINE ANALOGUES OF NUCLEOSIDASE AND PHOSPHORYLASE INHIBITORS". Page/Page column 25-26. . Retrieved 2008/12/07.