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

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Chemical Name:(2S,5R)-5-((S)-2-Bromo-1-triethylsilanyloxy-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester
CAS No.:182137-73-1
Molecular Formula:C₂₅H₄₀BrNO₅Si
Molecular Weight:542.586
Hs Code.:

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

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

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

There total 11 articles about (2S,5R)-5-((S)-2-Bromo-1-triethylsilanyloxy-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:

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

: 182137-73-1
(2S,5R)-5-((S)-2-Bromo-1-triethylsilanyloxy-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Guidance literature:: Multi-step reaction with 10 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: 100 percent / Et₃N / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) room temperature, 5 min

7: 95 percent / ethanol / 1.) reflux, 20 min, 2.) cool to room temperature, 35 min.

8: 1.) NaIO₄, 2.) H₂O₂, NMM / 1.) THF, H₂O, 55 deg C, 2.5 h, 2.) H₂O, heating, 3 h.

9: 27 percent / m-CPBA / CH₂Cl₂ / 1.) -10 - 4 deg C, 6 h, 2.) 4 deg C, 41 h.

10: 1.) PPh₃, Br₂, 2.) imidazole / 1.) CH₂Cl₂, 50 min, 2.) CH₂Cl₂, room temperature, 35 min.

With 4-methyl-morpholine; 1H-imidazole; 1-methyl-pyrrolidin-2-one; sodium periodate; lithium borohydride; hydrogen; dihydrogen peroxide; bromine; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium on activated charcoal; platinum on activated charcoal; In methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate;
DOI:10.1021/jo960759m

Reference yield:

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

: 182137-73-1
(2S,5R)-5-((S)-2-Bromo-1-triethylsilanyloxy-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Guidance literature:: Multi-step reaction with 9 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: 100 percent / Et₃N / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) room temperature, 5 min

6: 95 percent / ethanol / 1.) reflux, 20 min, 2.) cool to room temperature, 35 min.

7: 1.) NaIO₄, 2.) H₂O₂, NMM / 1.) THF, H₂O, 55 deg C, 2.5 h, 2.) H₂O, heating, 3 h.

8: 27 percent / m-CPBA / CH₂Cl₂ / 1.) -10 - 4 deg C, 6 h, 2.) 4 deg C, 41 h.

9: 1.) PPh₃, Br₂, 2.) imidazole / 1.) CH₂Cl₂, 50 min, 2.) CH₂Cl₂, room temperature, 35 min.

With 4-methyl-morpholine; 1H-imidazole; sodium periodate; lithium borohydride; hydrogen; dihydrogen peroxide; bromine; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium on activated charcoal; platinum on activated charcoal; In methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate;
DOI:10.1021/jo960759m

Reference yield:

: 90741-40-5
tert-butyl (2R,5R)-1-benzyl-5-(2-hydroxyethyl)pyrrolidine-2-carboxylate

: 182137-73-1
(2S,5R)-5-((S)-2-Bromo-1-triethylsilanyloxy-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

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

2: K₂CO₃ / ethyl acetate; H₂O / 1.5 h

3: 100 percent / Et₃N / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) room temperature, 5 min

4: 95 percent / ethanol / 1.) reflux, 20 min, 2.) cool to room temperature, 35 min.

5: 1.) NaIO₄, 2.) H₂O₂, NMM / 1.) THF, H₂O, 55 deg C, 2.5 h, 2.) H₂O, heating, 3 h.

6: 27 percent / m-CPBA / CH₂Cl₂ / 1.) -10 - 4 deg C, 6 h, 2.) 4 deg C, 41 h.

7: 1.) PPh₃, Br₂, 2.) imidazole / 1.) CH₂Cl₂, 50 min, 2.) CH₂Cl₂, room temperature, 35 min.

With 4-methyl-morpholine; 1H-imidazole; sodium periodate; hydrogen; dihydrogen peroxide; bromine; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; ethyl acetate;
DOI:10.1021/jo960759m