ethyl (2R,3R,4S)-2-(3-Fluoro-4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-pyrrolidine-3-carboxylate

Base Information

• Chemical Name: ethyl (2R,3R,4S)-2-(3-Fluoro-4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-pyrrolidine-3-carboxylate
• CAS No.: 195510-85-1
• Molecular Formula: C₂₁H₂₂FNO₅
• Molecular Weight: 387.408
• Mol file: 195510-85-1.mol

Synonyms:ethyl (2R,3R,4S)-2-(3-Fluoro-4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-pyrrolidine-3-carboxylate

Chemical Property of ethyl (2R,3R,4S)-2-(3-Fluoro-4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-pyrrolidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2R,3R,4S)-2-(3-Fluoro-4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-pyrrolidine-3-carboxylate

There total 17 articles about ethyl (2R,3R,4S)-2-(3-Fluoro-4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-pyrrolidine-3-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: 89.0%

ethanol (64-17-5) + (2R,3R,4S)-4-Benzo[1,3]dioxol-5-yl-2-(3-fluoro-4-methoxy-phenyl)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (195510-84-0) → ethyl (2R,3R,4S)-2-(3-Fluoro-4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-pyrrolidine-3-carboxylate (195510-85-1)

Guidance literature:

With hydrogenchloride; at 50 ℃; for 16h;

DOI:10.1021/jm970101g

Reference yield:

ethyl (3-fluoro-4-methoxybenzoyl)acetate (195708-39-5) → ethyl (2R,3R,4S)-2-(3-Fluoro-4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-pyrrolidine-3-carboxylate (195510-85-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: KO-tBu / tetrahydrofuran / 3.5 h / 20 °C

2.1: H₂ / RaNi / ethyl acetate / 4 h / 20 °C / 3102.97 Torr

2.2: TFA; H₂ / 24 h

3.1: DBU / toluene / 12 h / Heating

4.1: CH₂Cl₂ / 2 h / 20 °C

5.1: aq. NaOH / 2 h / 20 °C

6.1: diethyl ether

7.1: aq. HCl

With hydrogenchloride; sodium hydroxide; potassium tert-butylate; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; RaNi; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; toluene; 1.1: Michael addition / 7.1: Fischer esterification;

DOI:10.1021/jm010237l

Reference yield:

3-Benzo[1,3]dioxol-5-yl-2-(3-fluoro-4-methoxy-benzoyl)-4-nitro-butyric acid ethyl ester (220584-76-9) → ethyl (2R,3R,4S)-2-(3-Fluoro-4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)-pyrrolidine-3-carboxylate (195510-85-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: H₂ / RaNi / ethyl acetate / 4 h / 20 °C / 3102.97 Torr

1.2: TFA; H₂ / 24 h

2.1: DBU / toluene / 12 h / Heating

3.1: CH₂Cl₂ / 2 h / 20 °C

4.1: aq. NaOH / 2 h / 20 °C

5.1: diethyl ether

6.1: aq. HCl

With hydrogenchloride; sodium hydroxide; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; RaNi; In diethyl ether; dichloromethane; ethyl acetate; toluene; 6.1: Fischer esterification;

DOI:10.1021/jm010237l

upstream raw materials:

ethanol

(2R,3R,4S)-4-Benzo[1,3]dioxol-5-yl-2-(3-fluoro-4-methoxy-phenyl)-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester

piperonal

5-((E)-2-nitroethenyl)-1,3-benzodioxole

Downstream raw materials:

(2R,3R,4S)-4-Benzo[1,3]dioxol-5-yl-1-(2-bromo-ethyl)-2-(3-fluoro-4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester

(2R,3R,4S)-4-Benzo[1,3]dioxol-5-yl-2-(3-fluoro-4-methoxy-phenyl)-1-{2-[propyl-(4,4,4-trifluoro-butane-1-sulfonyl)-amino]-ethyl}-pyrrolidine-3-carboxylic acid ethyl ester

Ethyl (2R,3R,4S)2-(3-Fluoro-4-methoxyphenyl)-4-(1,3-benzodioxol-5-yl)1-(2-(N-propylamino)ethyl)-pyrrolidine-3-carboxylate

(2R,3R,4S)-4-Benzo[1,3]dioxol-5-yl-1-{2-[(butane-1-sulfonyl)-propyl-amino]-ethyl}-2-(3-fluoro-4-methoxy-phenyl)-pyrrolidine-3-carboxylic acid ethyl ester