tert-butyl (cis)-2,4-bis{[(4-methylbenzenesulfonyl)oxy]methyl}azetidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (cis)-2,4-bis{[(4-methylbenzenesulfonyl)oxy]methyl}azetidine-1-carboxylate
• CAS No.: 1414540-38-7
• Molecular Formula: C₂₄H₃₁NO₈S₂
• Molecular Weight: 525.644
• Mol file: 1414540-38-7.mol

Synonyms:tert-butyl (cis)-2,4-bis{[(4-methylbenzenesulfonyl)oxy]methyl}azetidine-1-carboxylate

Chemical Property of tert-butyl (cis)-2,4-bis{[(4-methylbenzenesulfonyl)oxy]methyl}azetidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (cis)-2,4-bis{[(4-methylbenzenesulfonyl)oxy]methyl}azetidine-1-carboxylate

There total 5 articles about tert-butyl (cis)-2,4-bis{[(4-methylbenzenesulfonyl)oxy]methyl}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:

diethyl (2R*,4R*)-1-benzylazetidine-2,4-dicarboxylate → tert-butyl (cis)-2,4-bis{[(4-methylbenzenesulfonyl)oxy]methyl}azetidine-1-carboxylate (1414540-38-7)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydride / N,N-dimethyl-formamide; toluene / 24 h / 80 °C

2: hydrogen; 10 wt% Pd(OH)2 on carbon

3: ethanol / 24 h / 3102.97 Torr

4: sodium tetrahydroborate; calcium chloride / methanol / 5 h / 0 - 10 °C

5: pyridine / 24 h / 0 - 20 °C

With pyridine; sodium tetrahydroborate; 10 wt% Pd(OH)2 on carbon; hydrogen; sodium hydride; calcium chloride; In methanol; ethanol; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tetlet.2012.08.156

Reference yield:

2,4-diethyl (2R,4S)-1-benzylazetidine-2,4-dicarboxylate (174309-28-5,1016233-19-4) → tert-butyl (cis)-2,4-bis{[(4-methylbenzenesulfonyl)oxy]methyl}azetidine-1-carboxylate (1414540-38-7)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogen; 10 wt% Pd(OH)2 on carbon

2: ethanol / 24 h / 3102.97 Torr

3: sodium tetrahydroborate; calcium chloride / methanol / 5 h / 0 - 10 °C

4: pyridine / 24 h / 0 - 20 °C

With pyridine; sodium tetrahydroborate; 10 wt% Pd(OH)2 on carbon; hydrogen; calcium chloride; In methanol; ethanol;

DOI:10.1016/j.tetlet.2012.08.156

Reference yield:

1-tert-butyl 2,4-diethyl cis-azetidine-1,2,4-tricarboxylate (1414540-31-0) → tert-butyl (cis)-2,4-bis{[(4-methylbenzenesulfonyl)oxy]methyl}azetidine-1-carboxylate (1414540-38-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate; calcium chloride / methanol / 5 h / 0 - 10 °C

2: pyridine / 24 h / 0 - 20 °C

With pyridine; sodium tetrahydroborate; calcium chloride; In methanol;

DOI:10.1016/j.tetlet.2012.08.156

upstream raw materials:

2,4-diethyl (2R,4S)-1-benzylazetidine-2,4-dicarboxylate

1-tert-butyl 2,4-diethyl cis-azetidine-1,2,4-tricarboxylate

2,4-dibromoglutaric acid diethyl ester

Downstream raw materials:

3,6-diazabicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester

3-[(2-nitrophenyl)sulfonyl]-3,6-diazabicyclo[3.1.1]heptane

tert-butyl 3-[(2-nitrophenyl)sulfonyl]-3,6-diazabicyclo[3.1.1]heptane-6-carboxylate

(1R,5S)-3-thia-6-azabicyclo[3.1.1]heptane 3,3-dioxide hydrotosylate