(2S,4S)-4-Cyclohexyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

Base Information

• Chemical Name: (2S,4S)-4-Cyclohexyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester
• CAS No.: 103201-84-9
• Molecular Formula: C₁₉H₂₅NO₄
• Molecular Weight: 331.412
• Mol file: 103201-84-9.mol

Synonyms:(2S,4S)-4-Cyclohexyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

Chemical Property of (2S,4S)-4-Cyclohexyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,4S)-4-Cyclohexyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

There total 9 articles about (2S,4S)-4-Cyclohexyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl 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:

(S)-Pyroglutaminol (17342-08-4) → (2S,4S)-4-Cyclohexyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (103201-84-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / TosOH / toluene / 9 h / Heating

2: 1.) LDA, / 1.) THF, -78 deg C, 30 min, 2.) THF, -20 deg C, 20 min

3: 100 percent / LAH / tetrahydrofuran / 1 h / Heating

4: 65 percent / H₂ / 10percentPd/C / ethyl acetate; acetic acid / 2 h / 2327.2 Torr

5: 77.9 g / aq.K₂CO₃ / tetrahydrofuran / 0.25 h / 0 °C

6: 78.4 g / aq.(CrO₃/H₂SO₄) / acetone / 3 h / -5 °C

With chromium(VI) oxide; lithium aluminium tetrahydride; sulfuric acid; hydrogen; potassium carbonate; toluene-4-sulfonic acid; lithium diisopropyl amide; 10% palladium on active carbon; In tetrahydrofuran; acetic acid; ethyl acetate; acetone; toluene;

DOI:10.1021/jo00366a011

Reference yield:

(2S-trans)-1-[(benzyloxy)carbonyl]-4-cyclohexyl-2-pyrrolidinemethanol (103201-83-8) → (2S,4S)-4-Cyclohexyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (103201-84-9)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In acetone; at -5 ℃; for 3h;

DOI:10.1021/jo00366a011

Reference yield:

(2R,SS)-2-phenyl-3-oxa-1-azabicyclo(3.3.0)octan-8-one (1217546-92-3,1820583-17-2) → (2S,4S)-4-Cyclohexyl-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester (103201-84-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) LDA, / 1.) THF, -78 deg C, 30 min, 2.) THF, -20 deg C, 20 min

2: 100 percent / LAH / tetrahydrofuran / 1 h / Heating

3: 65 percent / H₂ / 10percentPd/C / ethyl acetate; acetic acid / 2 h / 2327.2 Torr

4: 77.9 g / aq.K₂CO₃ / tetrahydrofuran / 0.25 h / 0 °C

5: 78.4 g / aq.(CrO₃/H₂SO₄) / acetone / 3 h / -5 °C

With chromium(VI) oxide; lithium aluminium tetrahydride; sulfuric acid; hydrogen; potassium carbonate; lithium diisopropyl amide; 10% palladium on active carbon; In tetrahydrofuran; acetic acid; ethyl acetate; acetone;

DOI:10.1021/jo00366a011

upstream raw materials:

(2S-trans)-1-[(benzyloxy)carbonyl]-4-cyclohexyl-2-pyrrolidinemethanol

benzyl chloroformate

trans-4-cyclohexyl-L-prolinol

(2R,SS)-2-phenyl-3-oxa-1-azabicyclo(3.3.0)octan-8-one

Downstream raw materials:

(2S,4S)-4-cyclohexylpyrrolidine-2-carboxylic acid

Refernces