1-Boc-3-allylazetidine

Base Information

• Chemical Name: 1-Boc-3-allylazetidine
• CAS No.: 206446-46-0
• Molecular Formula: C₁₁H₁₉NO₂
• Molecular Weight: 197.277
• Mol file: 206446-46-0.mol

Synonyms:1-Boc-3-allylazetidine;tert-butyl 3-(prop-2-en-1-yl)azetidine-1-carboxylate;tert-Butyl 3-allylazetidine-1-carboxylate

Chemical Property of 1-Boc-3-allylazetidine

Chemical Property:

• Boiling Point: 247.5±9.0 °C(Predicted)
• PKA: -1.38±0.40(Predicted)
• Density: 0.994±0.06 g/cm3(Predicted)

Purity/Quality:

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

1-Boc-3-allylazetidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Boc-3-allylazetidine

There total 4 articles about 1-Boc-3-allylazetidine 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: 65.0%

C13H26BO2(1-)*Li(1+) + tert-butyl-3-iodoazetidine-1-carboxylate (254454-54-1) → tert-butyl 3-allylazetidine-1-carboxylate (206446-46-0)

Guidance literature:

With tetrakis(actonitrile)copper(I) hexafluorophosphate; 2,2,6,6-tetramethylheptane-3,5-dione; trimethylsilyl(cumyl) peroxide; triethylamine; In tetrahydrofuran; dimethyl sulfoxide; at 20 ℃; for 1h; Sealed tube; Inert atmosphere;

DOI:10.1021/jacs.1c12649

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 3-allylazetidine-1-carboxylate (206446-46-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / Et₃N / CH₂Cl₂ / Ambient temperature

2: 75 percent / KI / dimethylsulfoxide / 140 °C

With triethylamine; potassium iodide; In dichloromethane; dimethyl sulfoxide;

DOI:10.1055/s-1998-37503

Reference yield:

3-methanesulfonyloxy-azetidine-1-carboxylic acid tert-butyl ester (141699-58-3) → tert-butyl 3-allylazetidine-1-carboxylate (206446-46-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / KI / dimethylsulfoxide / 140 °C

With potassium iodide; In dimethyl sulfoxide;

DOI:10.1055/s-1998-37503

upstream raw materials:

allyl bromide

tert-butyl-3-iodoazetidine-1-carboxylate

di-tert-butyl dicarbonate

3-methanesulfonyloxy-azetidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Billotte. "Synthesis of C-substituted cyclic amines using azacycloalkyl organozinc reagents". . p. 379 - 380. Retrieved 2007/10/03.