(1S,2S,3R)-methyl 2-(4-methoxyphenyl)bicyclo[1.1.0]butane-1-carboxylate

Base Information

• Chemical Name: (1S,2S,3R)-methyl 2-(4-methoxyphenyl)bicyclo[1.1.0]butane-1-carboxylate
• CAS No.: 1417719-53-9
• Molecular Formula: C₁₃H₁₄O₃
• Molecular Weight: 218.252
• Mol file: 1417719-53-9.mol

Synonyms:(1S,2S,3R)-methyl 2-(4-methoxyphenyl)bicyclo[1.1.0]butane-1-carboxylate

Chemical Property of (1S,2S,3R)-methyl 2-(4-methoxyphenyl)bicyclo[1.1.0]butane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R)-methyl 2-(4-methoxyphenyl)bicyclo[1.1.0]butane-1-carboxylate

There total 3 articles about (1S,2S,3R)-methyl 2-(4-methoxyphenyl)bicyclo[1.1.0]butane-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:

(E)-methyl 2-diazo-5-(4-methoxyphenyl)pent-4-enoate (1417719-44-8) → (1S,2S,3R)-methyl 2-(4-methoxyphenyl)bicyclo[1.1.0]butane-1-carboxylate (1417719-53-9) + (1R,2R,3S)-methyl 2-(4-methoxyphenyl)bicyclo[1.1.0]butane-1-carboxylate

Guidance literature:

With Rh₂(S-BTPCP)4; In ethyl acetate; at 20 ℃; for 0.75h; Overall yield = 66 %; Overall yield = 57.4 mg; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol303217s

Reference yield:

C15H18O4 (1417719-37-9) → (1S,2S,3R)-methyl 2-(4-methoxyphenyl)bicyclo[1.1.0]butane-1-carboxylate (1417719-53-9) + (1R,2R,3S)-methyl 2-(4-methoxyphenyl)bicyclo[1.1.0]butane-1-carboxylate

Guidance literature:

Multi-step reaction with 2 steps

1.1: 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C

2.1: Rh₂(S-BTPCP)4 / ethyl acetate / 0.75 h / 20 °C / Inert atmosphere

With 4-acetamidobenzenesulfonyl azide; Rh₂(S-BTPCP)4; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; ethyl acetate;

DOI:10.1021/ol303217s

Reference yield:

(E)-4-methoxycinnamyl bromide (90841-43-3,16034-99-4) → (1S,2S,3R)-methyl 2-(4-methoxyphenyl)bicyclo[1.1.0]butane-1-carboxylate (1417719-53-9) + (1R,2R,3S)-methyl 2-(4-methoxyphenyl)bicyclo[1.1.0]butane-1-carboxylate

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride; tetra-(n-butyl)ammonium iodide / 1,2-dimethoxyethane / 1 h / 0 °C / Inert atmosphere

1.2: 0 - 85 °C / Inert atmosphere

2.1: 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 0 °C / Inert atmosphere

2.2: 0 - 20 °C

3.1: Rh₂(S-BTPCP)4 / ethyl acetate / 0.75 h / 20 °C / Inert atmosphere

With 4-acetamidobenzenesulfonyl azide; Rh₂(S-BTPCP)4; tetra-(n-butyl)ammonium iodide; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,2-dimethoxyethane; dichloromethane; ethyl acetate;

DOI:10.1021/ol303217s

upstream raw materials:

C₁₅H₁₈O₄

(E)-4-methoxycinnamyl bromide

(E)-methyl 2-diazo-5-(4-methoxyphenyl)pent-4-enoate

Refernces