1-benzyl 2-ethyl(2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: 1-benzyl 2-ethyl(2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate
• CAS No.: 84062-29-3
• Molecular Formula: C₂₁H₂₃NO₄Se
• Molecular Weight: 432.378
• Mol file: 84062-29-3.mol

Synonyms:1-benzyl 2-ethyl(2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate

Chemical Property of 1-benzyl 2-ethyl(2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-benzyl 2-ethyl(2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate

There total 10 articles about 1-benzyl 2-ethyl(2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate 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%

ethanol (64-17-5) + diphenyl diselenide (1666-13-3) + methyl (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate (117811-78-6) → 1-benzyl 2-ethyl(2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate (84062-29-3)

Guidance literature:

With sodium tetrahydroborate; for 2h; Heating;

DOI:10.1021/jo00097a022

Reference yield:

methyl (2S,4R)-1-benzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylate (64187-48-0) → 1-benzyl 2-ethyl(2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate (84062-29-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 2 h

2: 90 percent / NaBH₄ / 2 h / Heating

With dmap; sodium tetrahydroborate; triethylamine; In dichloromethane;

DOI:10.1021/jo00097a022

Reference yield:

(R)-4-hydroxy-L-proline ethyl ester (1499-56-5,775275-31-5,790644-51-8,754962-86-2) → 1-benzyl 2-ethyl(2S,4S)-4-(phenylselanyl)pyrrolidine-1,2-dicarboxylate (84062-29-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 99 percent / Et₃N / tetrahydrofuran; H₂O / 12 h / Ambient temperature

2: 99 percent / Et₃N, DMAP / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 2 h

3: 90 percent / NaBH₄ / 2 h / Heating

With dmap; sodium tetrahydroborate; triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo00097a022

upstream raw materials:

ethanol

diphenyl diselenide

methyl (2S,4R)-1-benzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylate

N-<(phenylmethoxy)carbonyl>-4(R)-<<(4-methylphenyl)sulfonyl>oxy>-(S)-proline methyl ester

Downstream raw materials:

C₆₂H₈₉N₇O₁₅

(S)-2-{Methyl-[(R)-3-methyl-1-(2-trimethylsilanyl-ethoxycarbonyl)-butyl]-carbamoyl}-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester

N-Cbz-3,4-didehydro-L-prolyl-N-methyl-D-leucine

(S)-2,5-dihydro-pyrrole-1,2-dicarboxylic acid 1-benzyl ester