(2R,4S)-1-benzyloxycarbonyl-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2R,4S)-1-benzyloxycarbonyl-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylic acid
• CAS No.: 1418177-80-6
• Molecular Formula: C₂₀H₂₁NO₆
• Molecular Weight: 371.39

Synonyms:(2R,4S)-1-benzyloxycarbonyl-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylic acid

Chemical Property of (2R,4S)-1-benzyloxycarbonyl-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylic acid

Chemical Property:

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Technology Process of (2R,4S)-1-benzyloxycarbonyl-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylic acid

There total 3 articles about (2R,4S)-1-benzyloxycarbonyl-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-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: 80.0%

methyl (2R,4S)-1-benzyloxycarbonyl-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylate (1418177-74-8) → (2R,4S)-1-benzyloxycarbonyl-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylic acid (1418177-80-6)

Guidance literature:

With water; sodium hydroxide; In methanol; at 20 ℃; for 4h;

DOI:10.1016/j.bmc.2012.11.015

Reference yield:

(2R,4R)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate (155075-23-3) → (2R,4S)-1-benzyloxycarbonyl-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylic acid (1418177-80-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: chromic acid; sulfuric acid; water / acetone / 0.58 h / 20 °C

2.1: magnesium / tetrahydrofuran / 0.67 h

2.2: 1 h / 0 °C

2.3: 5.5 h / -60 °C

3.1: water; sodium hydroxide / methanol / 4 h / 20 °C

With sulfuric acid; water; chromic acid; magnesium; sodium hydroxide; In tetrahydrofuran; methanol; acetone; 1.1: |Jones Oxidation;

DOI:10.1016/j.bmc.2012.11.015

Reference yield:

methyl (2R)-1-benzyloxycarbonyl-4-oxopyrrolidine-2-carboxylate (132431-11-9) → (2R,4S)-1-benzyloxycarbonyl-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylic acid (1418177-80-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: magnesium / tetrahydrofuran / 0.67 h

1.2: 1 h / 0 °C

1.3: 5.5 h / -60 °C

2.1: water; sodium hydroxide / methanol / 4 h / 20 °C

With water; magnesium; sodium hydroxide; In tetrahydrofuran; methanol;

DOI:10.1016/j.bmc.2012.11.015

upstream raw materials:

methyl (2R)-1-benzyloxycarbonyl-4-oxopyrrolidine-2-carboxylate

(2R,4R)-1-benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

methyl (2R,4S)-1-benzyloxycarbonyl-4-hydroxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylate

Downstream raw materials:

C₁₂H₁₅NO₄

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