(2S,4S)-benzyl 2-(bis(3,5-bis(trifluoromethyl)phenyl)(hydroxy)methyl)-4-hydroxypyrrolidine-1-carboxylate

Base Information

• Chemical Name: (2S,4S)-benzyl 2-(bis(3,5-bis(trifluoromethyl)phenyl)(hydroxy)methyl)-4-hydroxypyrrolidine-1-carboxylate
• CAS No.: 1434302-11-0
• Molecular Formula: C₂₉H₂₁F₁₂NO₄
• Molecular Weight: 675.471

Synonyms:(2S,4S)-benzyl 2-(bis(3,5-bis(trifluoromethyl)phenyl)(hydroxy)methyl)-4-hydroxypyrrolidine-1-carboxylate

Chemical Property of (2S,4S)-benzyl 2-(bis(3,5-bis(trifluoromethyl)phenyl)(hydroxy)methyl)-4-hydroxypyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2S,4S)-benzyl 2-(bis(3,5-bis(trifluoromethyl)phenyl)(hydroxy)methyl)-4-hydroxypyrrolidine-1-carboxylate

There total 2 articles about (2S,4S)-benzyl 2-(bis(3,5-bis(trifluoromethyl)phenyl)(hydroxy)methyl)-4-hydroxypyrrolidine-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: 50.0%

3,6-bis(trifluoromethyl)bromobenzene (328-70-1) + 5-aza-5-carbobenzoxy-2-oxa-3-oxo-bicyclo<2.2.1>heptane (80986-14-7) → (2S,4S)-benzyl 2-(bis(3,5-bis(trifluoromethyl)phenyl)(hydroxy)methyl)-4-hydroxypyrrolidine-1-carboxylate (1434302-11-0)

Guidance literature:

3,6-bis(trifluoromethyl)bromobenzene; With magnesium; In tetrahydrofuran; for 0.5h; Inert atmosphere; Reflux;

5-aza-5-carbobenzoxy-2-oxa-3-oxo-bicyclo<2.2.1>heptane; In tetrahydrofuran; at 0 - 20 ℃; for 17h; Inert atmosphere;

DOI:10.1002/adsc.201200922

Reference yield:

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (13504-85-3) → (2S,4S)-benzyl 2-(bis(3,5-bis(trifluoromethyl)phenyl)(hydroxy)methyl)-4-hydroxypyrrolidine-1-carboxylate (1434302-11-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diethylazodicarboxylate; triphenylphosphine / toluene; tetrahydrofuran / 5 h / 0 - 20 °C / Inert atmosphere

2.1: magnesium / tetrahydrofuran / 0.5 h / Inert atmosphere; Reflux

2.2: 17 h / 0 - 20 °C / Inert atmosphere

With magnesium; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene;

DOI:10.1002/adsc.201200922

Reference yield: 65.0%

(2S,4S)-benzyl 2-(bis(3,5-bis(trifluoromethyl)phenyl)(hydroxy)methyl)-4-hydroxypyrrolidine-1-carboxylate (1434302-11-0) + dimethylsilicon dichloride (75-78-5,30107-43-8) → (1S,6S)-benzyl 5,5-bis(3,5-bis(trifluoromethyl)phenyl)-3,3-dimethyl-2,4-dioxa-7-aza-3-silabicyclo[4.2.1]nonane-7-carboxylate (1434302-14-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 19h; Inert atmosphere;

DOI:10.1002/adsc.201200922

upstream raw materials:

3,6-bis(trifluoromethyl)bromobenzene

5-aza-5-carbobenzoxy-2-oxa-3-oxo-bicyclo<2.2.1>heptane

(2S,4R)-1-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Downstream raw materials:

(1S,6S)-benzyl 5,5-bis(3,5-bis(trifluoromethyl)phenyl)-3,3-dimethyl-2,4-dioxa-7-aza-3-silabicyclo[4.2.1]nonane-7-carboxylate

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