2-[(1R,2S)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]ethyl 4-nitrobenzoate

Base Information

• Chemical Name: 2-[(1R,2S)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]ethyl 4-nitrobenzoate
• CAS No.: 55626-94-3
• Molecular Formula: C₁₇H₂₁NO₄
• Molecular Weight: 303.358
• Mol file: 55626-94-3.mol

Synonyms:2-[(1R,2S)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]ethyl 4-nitrobenzoate

Chemical Property of 2-[(1R,2S)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]ethyl 4-nitrobenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(1R,2S)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]ethyl 4-nitrobenzoate

There total 8 articles about 2-[(1R,2S)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]ethyl 4-nitrobenzoate 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: 41.0%

2-((2R)-2-methyl-2-{2-[(tetrahydro-2H-pyran-2-yl)oxy]ethyl}cyclobutyl)propan-2-ol + 4-nitro-benzoyl chloride (122-04-3) → 2-[(1R,2S)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]ethyl 4-nitrobenzoate (55626-94-3) + C17H21NO4

Guidance literature:

2-((2R)-2-methyl-2-{2-[(tetrahydro-2H-pyran-2-yl)oxy]ethyl}cyclobutyl)propan-2-ol; With thionyl chloride; at 0 - 5 ℃; for 2h; Inert atmosphere;

In methanol; at 20 - 25 ℃; for 14h; Inert atmosphere;

4-nitro-benzoyl chloride; With pyridine; dmap; In dichloromethane; at 20 - 25 ℃; for 2h; Inert atmosphere;

DOI:10.1002/ejoc.201801160

Reference yield:

2-((2S)-2-isocyano-2-{2-[(tetrahydro-2H-pyran-2-yl)oxy]ethyl}cyclobutyl)propan-2-ol → 2-[(1R,2S)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]ethyl 4-nitrobenzoate (55626-94-3) + C17H21NO4

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / toluene / 6 h / 0 - 25 °C / Inert atmosphere

2.1: hydrazine hydrate / diethylene glycol / 0.5 h / 200 - 205 °C / Inert atmosphere

2.2: 3 h / 200 - 205 °C / Inert atmosphere

3.1: thionyl chloride / 2 h / 0 - 5 °C / Inert atmosphere

3.2: Dowex 50Wx₈ / 14 h / 20 - 25 °C / Inert atmosphere

3.3: 2 h / 20 - 25 °C / Inert atmosphere

With thionyl chloride; diisobutylaluminium hydride; hydrazine hydrate; In toluene; diethylene glycol; 2.1: |Wolff-Kishner Reduction / 2.2: |Wolff-Kishner Reduction;

DOI:10.1002/ejoc.201801160

Reference yield:

(1S)-2-(2-hydroxypropan-2-yl)-1-{2-[(tetrahydro-2H-pyran-2-yl)oxy]-ethyl}cyclobutane-1-carbaldehyde → 2-[(1R,2S)-1-methyl-2-(prop-1-en-2-yl)cyclobutyl]ethyl 4-nitrobenzoate (55626-94-3) + C17H21NO4

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrazine hydrate / diethylene glycol / 0.5 h / 200 - 205 °C / Inert atmosphere

1.2: 3 h / 200 - 205 °C / Inert atmosphere

2.1: thionyl chloride / 2 h / 0 - 5 °C / Inert atmosphere

2.2: Dowex 50Wx₈ / 14 h / 20 - 25 °C / Inert atmosphere

2.3: 2 h / 20 - 25 °C / Inert atmosphere

With thionyl chloride; hydrazine hydrate; In diethylene glycol; 1.1: |Wolff-Kishner Reduction / 1.2: |Wolff-Kishner Reduction;

DOI:10.1002/ejoc.201801160

upstream raw materials:

4-nitro-benzoyl chloride

5-iodo-2-methylpent-2-ene

6-methylhept-5-enenitrile

Downstream raw materials:

(1R, 2S)-grandisol