(-)-tert-butyl (2S,3R)-1-benzyl-2-phenylpyrrolidine-3-carboxylate

Base Information

• Chemical Name: (-)-tert-butyl (2S,3R)-1-benzyl-2-phenylpyrrolidine-3-carboxylate
• CAS No.: 1394979-11-3
• Molecular Formula: C₂₂H₂₇NO₂
• Molecular Weight: 337.462
• Mol file: 1394979-11-3.mol

Synonyms:(-)-tert-butyl (2S,3R)-1-benzyl-2-phenylpyrrolidine-3-carboxylate

Chemical Property of (-)-tert-butyl (2S,3R)-1-benzyl-2-phenylpyrrolidine-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (-)-tert-butyl (2S,3R)-1-benzyl-2-phenylpyrrolidine-3-carboxylate

There total 4 articles about (-)-tert-butyl (2S,3R)-1-benzyl-2-phenylpyrrolidine-3-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: 97.0%

ethyleneglycol sulfate (1072-53-3) + tert-butyl cinnamate (14990-09-1) + C12H20NSi(1-)*Li(1+) → (-)-tert-butyl (2S,3R)-1-benzyl-2-phenylpyrrolidine-3-carboxylate (1394979-11-3)

Guidance literature:

C₁₂H₂₀NSi^(1-)*Li⁽¹⁺⁾; With (1S,2S)-1,2-dimethoxy-1,2-diphenylethane; In toluene; at -78 ℃; for 0.583333h;

tert-butyl cinnamate; In toluene; at -78 ℃; for 1.63h;

ethyleneglycol sulfate; enantioselective reaction; Further stages;

DOI:10.1021/jo301495a

Reference yield: 97.0%

tert-butyl cinnamate (14990-09-1) + Lithium N-benzyl-N-(trimethylsilyl)amide (113709-50-5) + 1-Bromo-2-chloroethane (107-04-0) → (R)-tert-butyl 3-(benzylamino)-2-deuterio-3-phenylpropanoate + (-)-tert-butyl (2S,3R)-1-benzyl-2-phenylpyrrolidine-3-carboxylate (1394979-11-3)

Guidance literature:

Lithium N-benzyl-N-(trimethylsilyl)amide; With (1S,2S)-1,2-dimethoxy-1,2-diphenylethane; In toluene; at -78 ℃; for 0.583333h;

tert-butyl cinnamate; In toluene; at -78 ℃; for 1.63h;

1-Bromo-2-chloroethane; Further stages;

DOI:10.1021/jo301495a

Reference yield: 27.0%

tert-butyl cinnamate (14990-09-1) + Lithium N-benzyl-N-(trimethylsilyl)amide (113709-50-5) + 1-Bromo-2-chloroethane (107-04-0) → tert-butyl (3S)-3-(benzylamino)-3-phenylpropanoate (190003-04-4) + (-)-tert-butyl (2S,3R)-1-benzyl-2-phenylpyrrolidine-3-carboxylate (1394979-11-3)

Guidance literature:

tert-butyl cinnamate; Lithium N-benzyl-N-(trimethylsilyl)amide; With (1S,2S)-1,2-dimethoxy-1,2-diphenylethane; In toluene; at -78 ℃; for 1.5h;

1-Bromo-2-chloroethane; In toluene; at -40 ℃; for 22h; Further stages;

DOI:10.1021/jo301495a

upstream raw materials:

tert-butyl cinnamate

Lithium N-benzyl-N-(trimethylsilyl)amide

1-Bromo-2-chloroethane

ethyleneglycol sulfate