tert-butyl 2-{4-[4-(methanesulfonyl)phenoxy]butyl}-7-azaspiro[3.5]nonane-7-carboxylate

Base Information

• Chemical Name: tert-butyl 2-{4-[4-(methanesulfonyl)phenoxy]butyl}-7-azaspiro[3.5]nonane-7-carboxylate
• CAS No.: 1416173-76-6
• Molecular Formula: C₂₄H₃₇NO₅S
• Molecular Weight: 451.627
• Mol file: 1416173-76-6.mol

Synonyms:tert-butyl 2-{4-[4-(methanesulfonyl)phenoxy]butyl}-7-azaspiro[3.5]nonane-7-carboxylate

Chemical Property of tert-butyl 2-{4-[4-(methanesulfonyl)phenoxy]butyl}-7-azaspiro[3.5]nonane-7-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 2-{4-[4-(methanesulfonyl)phenoxy]butyl}-7-azaspiro[3.5]nonane-7-carboxylate

There total 16 articles about tert-butyl 2-{4-[4-(methanesulfonyl)phenoxy]butyl}-7-azaspiro[3.5]nonane-7-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: 92.0%

4-methanesulfonyl-phenol (14763-60-1) + tert-butyl 2-(4-hydroxybutyl)-7-azaspiro[3.5]nonane-7-carboxylate → tert-butyl 2-{4-[4-(methanesulfonyl)phenoxy]butyl}-7-azaspiro[3.5]nonane-7-carboxylate (1416173-76-6)

Guidance literature:

With tributylphosphine; diamide; In tetrahydrofuran; at 60 ℃;

DOI:10.1016/j.bmc.2018.02.032

Reference yield: 83.0%

tert-butyl 2-(4-(4-(methylthio)phenoxy)butyl)-7-azaspiro[3.5]nonane-7-carboxylate → tert-butyl 2-{4-[4-(methanesulfonyl)phenoxy]butyl}-7-azaspiro[3.5]nonane-7-carboxylate (1416173-76-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1021/jacs.0c11964

Reference yield:

tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate (203661-69-2) → tert-butyl 2-{4-[4-(methanesulfonyl)phenoxy]butyl}-7-azaspiro[3.5]nonane-7-carboxylate (1416173-76-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / Cooling with ice

1.2: 3 h / 20 °C

2.1: hydrogen; 20% palladium hydroxide-activated charcoal / ethanol / 20 °C

3.1: lithium borohydride / tetrahydrofuran / 5 h / Reflux

4.1: Dess-Martin periodane / chloroform / 2 h / 20 °C

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / Cooling with ice

5.2: 3 h / 20 °C

6.1: hydrogen; 20% palladium hydroxide-activated charcoal / ethanol / 20 °C

7.1: lithium borohydride / tetrahydrofuran / 60 °C

8.1: diamide; tributylphosphine / tetrahydrofuran / 60 °C

With lithium borohydride; tributylphosphine; diamide; 20% palladium hydroxide-activated charcoal; hydrogen; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; ethanol; chloroform; N,N-dimethyl-formamide; mineral oil; 1.1: |Horner-Wadsworth-Emmons Olefination / 1.2: |Horner-Wadsworth-Emmons Olefination / 5.1: |Horner-Wadsworth-Emmons Olefination / 5.2: |Horner-Wadsworth-Emmons Olefination / 8.1: |Mitsunobu Displacement;

DOI:10.1016/j.bmc.2018.02.032

upstream raw materials:

tert-butyl 2-oxo-7-azaspiro[3.5]nonane-7-carboxylate

tert-butyl 2-(2-ethoxy-2-oxoethylidene)-7-azaspiro[3.5]nonane-7-carboxylate

tert-butyl 2-(2-ethoxy-2-oxoethyl)-7-azaspiro[3.5]nonane-7-carboxylate

4-methanesulfonyl-phenol