(2S,3S,4S)-3-(2-Hydroxy-ethyl)-4-(4-methoxy-phenyl)-pyrrolidine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester

Base Information

• Chemical Name: (2S,3S,4S)-3-(2-Hydroxy-ethyl)-4-(4-methoxy-phenyl)-pyrrolidine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester
• CAS No.: 135388-22-6
• Molecular Formula: C₁₈H₂₅NO₆
• Molecular Weight: 351.4

Synonyms:

Chemical Property of (2S,3S,4S)-3-(2-Hydroxy-ethyl)-4-(4-methoxy-phenyl)-pyrrolidine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-3-(2-Hydroxy-ethyl)-4-(4-methoxy-phenyl)-pyrrolidine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester

There total 17 articles about (2S,3S,4S)-3-(2-Hydroxy-ethyl)-4-(4-methoxy-phenyl)-pyrrolidine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl 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:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → (2S,3S,4S)-3-(2-Hydroxy-ethyl)-4-(4-methoxy-phenyl)-pyrrolidine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester (135388-22-6)

Guidance literature:

Multi-step reaction with 16 steps

1: Et₃N

2: imidazole

3: TFA

4: 1) tBuOCl, 2) Et₃N

5: pyridine

6: 70 percent / TBAF

7: 100 percent / N,N-dimethylaniline

8: 100 percent / nBu₃SnH, AIBN / benzene / Heating

9: DBU / toluene / Heating

10: Jones-oxidation

11: 94 percent / BH₃-Me₂S / tetrahydrofuran / 0 deg C to r.t.

12: 65 percent / Et₃N, DMAP

13: 86 percent / pyridine

14: H₂ / Pd/C

15: TBAF

With pyridine; 1H-imidazole; dmap; tert-butylhypochlorite; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; N,N-dimethyl-aniline; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; toluene; benzene;

DOI:10.1016/S0040-4039(00)78802-2

Reference yield:

N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester (89813-47-8) → (2S,3S,4S)-3-(2-Hydroxy-ethyl)-4-(4-methoxy-phenyl)-pyrrolidine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester (135388-22-6)

Guidance literature:

Multi-step reaction with 15 steps

1: imidazole

2: TFA

3: 1) tBuOCl, 2) Et₃N

4: pyridine

5: 70 percent / TBAF

6: 100 percent / N,N-dimethylaniline

7: 100 percent / nBu₃SnH, AIBN / benzene / Heating

8: DBU / toluene / Heating

9: Jones-oxidation

10: 94 percent / BH₃-Me₂S / tetrahydrofuran / 0 deg C to r.t.

11: 65 percent / Et₃N, DMAP

12: 86 percent / pyridine

13: H₂ / Pd/C

14: TBAF

With pyridine; 1H-imidazole; dmap; tert-butylhypochlorite; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; N,N-dimethyl-aniline; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; toluene; benzene;

DOI:10.1016/S0040-4039(00)78802-2

Reference yield:

(R)-4-(tert-Butyl-dimethyl-silanyloxy)-4,5-dihydro-3H-pyrrole-2-carboxylic acid benzyl ester (126891-22-3) → (2S,3S,4S)-3-(2-Hydroxy-ethyl)-4-(4-methoxy-phenyl)-pyrrolidine-1,2-dicarboxylic acid 1-ethyl ester 2-methyl ester (135388-22-6)

Guidance literature:

Multi-step reaction with 12 steps

1: pyridine

2: 70 percent / TBAF

3: 100 percent / N,N-dimethylaniline

4: 100 percent / nBu₃SnH, AIBN / benzene / Heating

5: DBU / toluene / Heating

6: Jones-oxidation

7: 94 percent / BH₃-Me₂S / tetrahydrofuran / 0 deg C to r.t.

8: 65 percent / Et₃N, DMAP

9: 86 percent / pyridine

10: H₂ / Pd/C

11: TBAF

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; N,N-dimethyl-aniline; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In tetrahydrofuran; toluene; benzene;

DOI:10.1016/S0040-4039(00)78802-2

upstream raw materials:

diazomethane

(2S,3R,4R)-3-(2-Hydroxy-ethyl)-4-(toluene-4-sulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-ethyl ester

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester

Downstream raw materials:

(2S,3S,4S)-3-methylenecarboxy-4-(4-methoxyphenyl)pyrrolidine-2-carboxylic acid

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