(3'R,4'S)-tert-butyl 3'-acetoxy-4'-{{6''-[benzyl(tert-butoxycarbonyl)amino]-4''-methylpyridin-2''-yl}methyl}pyrrolidine-1'-carboxylate

Base Information

Chemical Name:(3'R,4'S)-tert-butyl 3'-acetoxy-4'-{{6''-[benzyl(tert-butoxycarbonyl)amino]-4''-methylpyridin-2''-yl}methyl}pyrrolidine-1'-carboxylate
CAS No.:1018909-85-7
Molecular Formula:C₃₀H₄₁N₃O₆
Molecular Weight:539.672
Hs Code.:

Synonyms:(3'R,4'S)-tert-butyl 3'-acetoxy-4'-{{6''-[benzyl(tert-butoxycarbonyl)amino]-4''-methylpyridin-2''-yl}methyl}pyrrolidine-1'-carboxylate

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Chemical Property of (3'R,4'S)-tert-butyl 3'-acetoxy-4'-{{6''-[benzyl(tert-butoxycarbonyl)amino]-4''-methylpyridin-2''-yl}methyl}pyrrolidine-1'-carboxylate

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Technology Process of (3'R,4'S)-tert-butyl 3'-acetoxy-4'-{{6''-[benzyl(tert-butoxycarbonyl)amino]-4''-methylpyridin-2''-yl}methyl}pyrrolidine-1'-carboxylate

There total 7 articles about (3'R,4'S)-tert-butyl 3'-acetoxy-4'-{{6''-[benzyl(tert-butoxycarbonyl)amino]-4''-methylpyridin-2''-yl}methyl}pyrrolidine-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: 98.0%

: 1018909-83-5
(3'S,4'S)-tert-butyl 3'-{{6''-[benzyl(tert-butoxycarbonyl)-amino]-4''-methylpyridin-2''-yl}methyl}-4'-hydroxypyrrolidine-1'carboxylate

: 64-19-7,77671-22-8
acetic acid

: 1018909-85-7
(3'R,4'S)-tert-butyl 3'-acetoxy-4'-{{6''-[benzyl(tert-butoxycarbonyl)amino]-4''-methylpyridin-2''-yl}methyl}pyrrolidine-1'-carboxylate

Guidance literature:: (3'S,4'S)-tert-butyl 3'-{{6''-[benzyl(tert-butoxycarbonyl)-amino]-4''-methylpyridin-2''-yl}methyl}-4'-hydroxypyrrolidine-1'carboxylate; With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 0.333333h; N₂ atmosphere;

acetic acid; In tetrahydrofuran; at 20 ℃; for 48h;
DOI:10.1021/ja910228a

Reference yield:

: trans-[6-(1-benzyl-4-hydroxy-pyrrolidin-3-ylmethyl)-4-methyl-pyridin-2-yl]-carbamic acid tert-butyl ester

: 1018909-85-7
(3'R,4'S)-tert-butyl 3'-acetoxy-4'-{{6''-[benzyl(tert-butoxycarbonyl)amino]-4''-methylpyridin-2''-yl}methyl}pyrrolidine-1'-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C

1.2: 0 - 20 °C

2.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 °C

3.1: methanol; sodium hydroxide; water / 20 °C

3.2: pH 7

4.1: dmap; triethylamine / dichloromethane / 7 h / 0 - 20 °C

5.1: methanol; water

6.1: methanol; water; sodium carbonate / 14 h / 20 °C

7.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.33 h / 0 °C

7.2: 48 h / 0 - 20 °C

With methanol; dmap; sodium hydroxide; di-isopropyl azodicarboxylate; water; sodium hydride; sodium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

: (+/-)-cis-tert-butyl 3-{{6'-[benzyl(tert-butoxycarbonyl)amino]-4'-methylpyridin-2'-yl}methyl}-4-hydroxypyrrolidine-1-carboxylate

: 1018909-85-7
(3'R,4'S)-tert-butyl 3'-acetoxy-4'-{{6''-[benzyl(tert-butoxycarbonyl)amino]-4''-methylpyridin-2''-yl}methyl}pyrrolidine-1'-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: dmap; triethylamine / dichloromethane / 7 h / 0 - 20 °C

2.1: methanol; water

3.1: methanol; water; sodium carbonate / 14 h / 20 °C

4.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.33 h / 0 °C

4.2: 48 h / 0 - 20 °C

With methanol; dmap; di-isopropyl azodicarboxylate; water; sodium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water;