(2R,4S)-1-ethoxycarbonyl-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]-4-(p-toluenesulfonyloxy)pyrrolidine

Base Information

Chemical Name:(2R,4S)-1-ethoxycarbonyl-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]-4-(p-toluenesulfonyloxy)pyrrolidine
CAS No.:318511-31-8
Molecular Formula:C₃₁H₃₇NO₇S
Molecular Weight:567.703
Hs Code.:

Synonyms:(2R,4S)-1-ethoxycarbonyl-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]-4-(p-toluenesulfonyloxy)pyrrolidine

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Chemical Property of (2R,4S)-1-ethoxycarbonyl-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]-4-(p-toluenesulfonyloxy)pyrrolidine

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Technology Process of (2R,4S)-1-ethoxycarbonyl-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]-4-(p-toluenesulfonyloxy)pyrrolidine

There total 7 articles about (2R,4S)-1-ethoxycarbonyl-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]-4-(p-toluenesulfonyloxy)pyrrolidine 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: 83.0%

: 4124-41-8
p-toluenesulfonylanhydride

: 318511-30-7
(2R,4S)-1-ethoxycarbonyl-4-hydroxy-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]pyrrolidine

: 318511-31-8
(2R,4S)-1-ethoxycarbonyl-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]-4-(p-toluenesulfonyloxy)pyrrolidine

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃;
DOI:10.1248/cpb.48.1729

Reference yield:

: 318511-16-9
(2R,4R)-4-benzyloxy-1-ethoxycarbonyl-2-(2-hydroxyethyl)pyrrolidine

: 318511-31-8
(2R,4S)-1-ethoxycarbonyl-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]-4-(p-toluenesulfonyloxy)pyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: 80 percent / Et₃N / CH₂Cl₂ / 2.5 h / 20 °C

2.1: t-BuOK / N,N-dimethyl-acetamide / 0.17 h / 0 °C

2.2: 80 percent / N,N-dimethyl-acetamide / 4 h / 20 °C

3.1: 93 percent / H₂ / 5 percent Pd/C / ethanol / 7 h / 60 °C

4.1: 95 percent / diethyl azodicarboxylate; Ph₃P / CH₂Cl₂ / 15 h / 20 °C

5.1: 99 percent / LiBH₄ / tetrahydrofuran / 26.5 h / 20 - 40 °C

6.1: 83 percent / Et₃N / CH₂Cl₂ / 20 °C

With lithium borohydride; potassium tert-butylate; hydrogen; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl acetamide; 4.1: Mitsunobu reaction;
DOI:10.1248/cpb.48.1729

Reference yield:

: 318511-15-8
(2S,4R)-4-benzyloxy-1-ethoxycarbonyl-2-(ethoxycarbonylmethyl)pyrrolidine

: 318511-31-8
(2R,4S)-1-ethoxycarbonyl-2-[2-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]ethyl]-4-(p-toluenesulfonyloxy)pyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1.1: 85 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / -10 °C

2.1: 80 percent / Et₃N / CH₂Cl₂ / 2.5 h / 20 °C

3.1: t-BuOK / N,N-dimethyl-acetamide / 0.17 h / 0 °C

3.2: 80 percent / N,N-dimethyl-acetamide / 4 h / 20 °C

4.1: 93 percent / H₂ / 5 percent Pd/C / ethanol / 7 h / 60 °C

5.1: 95 percent / diethyl azodicarboxylate; Ph₃P / CH₂Cl₂ / 15 h / 20 °C

6.1: 99 percent / LiBH₄ / tetrahydrofuran / 26.5 h / 20 - 40 °C

7.1: 83 percent / Et₃N / CH₂Cl₂ / 20 °C

With lithium aluminium tetrahydride; lithium borohydride; potassium tert-butylate; hydrogen; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl acetamide; 5.1: Mitsunobu reaction;
DOI:10.1248/cpb.48.1729