3-Cyano-3-methyl-azetidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 3-Cyano-3-methyl-azetidine-1-carboxylic acid tert-butyl ester
• CAS No.: 936850-09-8
• Molecular Formula: C₁₀H₁₆N₂O₂
• Molecular Weight: 196.249
• Hs Code.: 2933990090
• Mol file: 936850-09-8.mol

Synonyms:3-Cyano-3-methyl-azetidine-1-carboxylic acid tert-butyl ester;1-Boc-3-cyano-3-Methylaze...;1-Boc-3-cyano-3-Methylazetidine;tert-butyl 3-cyano-3-Methylazetidine-1-carboxylate;3-Cyano-3-methyl-1-azetidinecarboxylic acid tert-butyl ester

Chemical Property of 3-Cyano-3-methyl-azetidine-1-carboxylic acid tert-butyl ester

Chemical Property:

• Boiling Point: 292℃
• Flash Point: 130℃
• PSA: 53.33000
• Density: 1.09
• LogP: 1.70488
• Storage Temp.: 2-8°C

Purity/Quality:

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

1-Boc-3-cyano-3-methylazetidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Cyano-3-methyl-azetidine-1-carboxylic acid tert-butyl ester

There total 3 articles about 3-Cyano-3-methyl-azetidine-1-carboxylic acid tert-butyl ester 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: 89.0%

tert-butyl 3-cyanoazetidine-1-carboxylate (142253-54-1) + methyl iodide (74-88-4) → tert-butyl 3-cyano-3-methylazetidine-1-carboxylate (936850-09-8)

Guidance literature:

tert-butyl 3-cyanoazetidine-1-carboxylate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -76 ℃; for 0.916667h;

methyl iodide; In tetrahydrofuran; at -76 - 20 ℃; for 1.5h; Product distribution / selectivity;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 3-cyano-3-methylazetidine-1-carboxylate (936850-09-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 16 h

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.92 h / -76 °C

2.2: 1.5 h / -76 - 20 °C

With triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

Reference yield:

tert-butyl-3-iodoazetidine-1-carboxylate (254454-54-1) → tert-butyl 3-cyano-3-methylazetidine-1-carboxylate (936850-09-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dimethyl sulfoxide / 6 h / 130 °C

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

2.2: 1.75 h / -78 - 24 °C

With lithium hexamethyldisilazane; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.24820/ark.5550190.p010.549

upstream raw materials:

tert-butyl 3-cyanoazetidine-1-carboxylate

methyl iodide

di-tert-butyl dicarbonate

tert-butyl-3-iodoazetidine-1-carboxylate

Downstream raw materials:

1-[(tert-butoxy)carbonyl]-3-methylazetidine-3-carboxylic acid

3-methylazetidine-3-carbonitrile hydrochloride

Refernces

• 1、 -. "CYTOMEGALOVIRUS INHIBITOR COMPOUNDS". Page/Page column 27; 28. . Retrieved 2013/10/22.
• 2、 -. "DIHYDROPYRROLONAPHTYRIDINONE COMPOUNDS AS INHIBITORS OF JAK". Page/Page column 97-98. . Retrieved 2010/12/29.