(2R,3R,4S)-1-(tert-butoxycarbonyl)-4-(benzo[d][1,3]dioxol-6-yl)-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid

Base Information

Chemical Name:(2R,3R,4S)-1-(tert-butoxycarbonyl)-4-(benzo[d][1,3]dioxol-6-yl)-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid
CAS No.:209214-30-2
Molecular Formula:C₂₄H₂₇NO₇
Molecular Weight:441.481
Hs Code.:

Synonyms:(2R,3R,4S)-1-(tert-butoxycarbonyl)-4-(benzo[d][1,3]dioxol-6-yl)-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid

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Chemical Property of (2R,3R,4S)-1-(tert-butoxycarbonyl)-4-(benzo[d][1,3]dioxol-6-yl)-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid

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Technology Process of (2R,3R,4S)-1-(tert-butoxycarbonyl)-4-(benzo[d][1,3]dioxol-6-yl)-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid

There total 12 articles about (2R,3R,4S)-1-(tert-butoxycarbonyl)-4-(benzo[d][1,3]dioxol-6-yl)-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid 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: 61.0%

: (2R,3R,4S)-4-Benzo[1,3]dioxol-5-yl-3-((S)-4-benzyl-2-oxo-oxazolidine-3-carbonyl)-2-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 209214-30-2
(2R,3R,4S)-1-(tert-butoxycarbonyl)-4-(benzo[d][1,3]dioxol-6-yl)-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid

Guidance literature:: (2R,3R,4S)-4-Benzo[1,3]dioxol-5-yl-3-((S)-4-benzyl-2-oxo-oxazolidine-3-carbonyl)-2-(4-methoxy-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester; With dihydrogen peroxide; lithium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 0.5h;

With citric acid; In water;

Reference yield:

: 1485-00-3,22568-48-5
5-((E)-2-nitroethenyl)-1,3-benzodioxole

: 209214-30-2
(2R,3R,4S)-1-(tert-butoxycarbonyl)-4-(benzo[d][1,3]dioxol-6-yl)-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 78 percent / DBU / tetrahydrofuran; propan-2-ol / 4 h / Ambient temperature

2: 12.34 g / H₂ / Raney nickel / ethanol / 3040 Torr

3: 1.) sodium cyanoborohydride, 2.) bromocresol green, conc. HCl / 1.) THF, EtOH, 2.) THF, EtOH, 20 min

4: 2.775 g / C₂H₅ONa / ethanol / Heating

5: 91 percent / CH₂Cl₂ / 1 h / Ambient temperature

6: 95 percent / NaOH

With hydrogenchloride; sodium hydroxide; hydrogen; sodium ethanolate; bromocresol green; sodium cyanoborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; nickel; In tetrahydrofuran; ethanol; dichloromethane; isopropyl alcohol;
DOI:10.1021/jm9505369

Reference yield:

: 173864-45-4
Ethyl 2-(4-methoxybenzoyl)-3-(3.4-methylenedioxy-phenyl)-4-nitro-butanoate

: 209214-30-2
(2R,3R,4S)-1-(tert-butoxycarbonyl)-4-(benzo[d][1,3]dioxol-6-yl)-2-(4-methoxyphenyl)pyrrolidine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 12.34 g / H₂ / Raney nickel / ethanol / 3040 Torr

2: 1.) sodium cyanoborohydride, 2.) bromocresol green, conc. HCl / 1.) THF, EtOH, 2.) THF, EtOH, 20 min

3: 2.775 g / C₂H₅ONa / ethanol / Heating

4: 91 percent / CH₂Cl₂ / 1 h / Ambient temperature

5: 95 percent / NaOH

With hydrogenchloride; sodium hydroxide; hydrogen; sodium ethanolate; bromocresol green; sodium cyanoborohydride; nickel; In ethanol; dichloromethane;
DOI:10.1021/jm9505369