(2S,5R)-5-(2-Bromo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

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Chemical Name:(2S,5R)-5-(2-Bromo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester
CAS No.:182137-38-8
Molecular Formula:C₁₉H₂₆BrNO₄
Molecular Weight:412.324
Hs Code.:

Synonyms:(2S,5R)-5-(2-Bromo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

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Chemical Property of (2S,5R)-5-(2-Bromo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

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Technology Process of (2S,5R)-5-(2-Bromo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

There total 7 articles about (2S,5R)-5-(2-Bromo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 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: 90.0%

: 178813-40-6
(2S,5R)-5-(2-Hydroxy-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

: 182137-38-8
(2S,5R)-5-(2-Bromo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Guidance literature:: With carbon tetrabromide; triphenylphosphine; In dichloromethane; Ambient temperature; 1.) -5 - 4 deg C, 1.75 h, 2.) 4 deg C - room temperature, 2 h, 3.) room temperatute, 2 h.;
DOI:10.1021/jo960759m

Reference yield:

: 90741-31-4
(S)-N-benzyl-5-thioxoproline tert-butyl ester

: 182137-38-8
(2S,5R)-5-(2-Bromo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 2.) Ph₃P, NMP / 1.) CH₃CN, 42 h, 2.) CH₂Cl₂, -5 deg C, 30 h.

2: 98 percent / H₂ / Pt/C / ethyl acetate / 16 h / 3102.9 Torr

3: 94 percent / LiBH₄ / diethyl ether / 4.5 h

4: H₂ / Pd/C / methanol / 12 h / 3102.9 Torr

5: K₂CO₃ / ethyl acetate; H₂O / 1.5 h

6: 90 percent / CBr₄, Ph₃P / CH₂Cl₂ / Ambient temperature; 1.) -5 - 4 deg C, 1.75 h, 2.) 4 deg C - room temperature, 2 h, 3.) room temperatute, 2 h.

With 1-methyl-pyrrolidin-2-one; lithium borohydride; carbon tetrabromide; hydrogen; potassium carbonate; triphenylphosphine; palladium on activated charcoal; platinum on activated charcoal; In methanol; diethyl ether; dichloromethane; water; ethyl acetate;
DOI:10.1021/jo960759m

Reference yield:

: 90741-33-6
(2S)-1-benzyl-(E)-5-<(methoxycarbonyl)methylidene>proline tert-butyl ester

: 182137-38-8
(2S,5R)-5-(2-Bromo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / H₂ / Pt/C / ethyl acetate / 16 h / 3102.9 Torr

2: 94 percent / LiBH₄ / diethyl ether / 4.5 h

3: H₂ / Pd/C / methanol / 12 h / 3102.9 Torr

4: K₂CO₃ / ethyl acetate; H₂O / 1.5 h

5: 90 percent / CBr₄, Ph₃P / CH₂Cl₂ / Ambient temperature; 1.) -5 - 4 deg C, 1.75 h, 2.) 4 deg C - room temperature, 2 h, 3.) room temperatute, 2 h.

With lithium borohydride; carbon tetrabromide; hydrogen; potassium carbonate; triphenylphosphine; palladium on activated charcoal; platinum on activated charcoal; In methanol; diethyl ether; dichloromethane; water; ethyl acetate;
DOI:10.1021/jo960759m