(2S,3S,4S)-3-Methoxycarbonylmethyl-4-(2-methoxy-phenyl)-pyrrolidine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S,4S)-3-Methoxycarbonylmethyl-4-(2-methoxy-phenyl)-pyrrolidine-2-carboxylic acid methyl ester
• CAS No.: 126891-21-2
• Molecular Formula: C₁₆H₂₁NO₅
• Molecular Weight: 307.346
• Mol file: 126891-21-2.mol

Synonyms:

Chemical Property of (2S,3S,4S)-3-Methoxycarbonylmethyl-4-(2-methoxy-phenyl)-pyrrolidine-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-3-Methoxycarbonylmethyl-4-(2-methoxy-phenyl)-pyrrolidine-2-carboxylic acid methyl ester

There total 21 articles about (2S,3S,4S)-3-Methoxycarbonylmethyl-4-(2-methoxy-phenyl)-pyrrolidine-2-carboxylic acid 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-Methoxycarbonylmethyl-4-(2-methoxy-phenyl)-pyrrolidine-2-carboxylic acid methyl ester (126891-21-2)

Guidance literature:

Multi-step reaction with 19 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

17: PDC / dimethylformamide

19: H₂, KOH

With pyridine; 1H-imidazole; dmap; potassium hydroxide; dipyridinium dichromate; 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; N,N-dimethyl-formamide; 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-Methoxycarbonylmethyl-4-(2-methoxy-phenyl)-pyrrolidine-2-carboxylic acid methyl ester (126891-21-2)

Guidance literature:

Multi-step reaction with 18 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

16: PDC / dimethylformamide

18: H₂, KOH

With pyridine; 1H-imidazole; dmap; potassium hydroxide; dipyridinium dichromate; 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; N,N-dimethyl-formamide; toluene; benzene;

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

Reference yield:

(2S,4R)-4-tert-butyldimethylsiloxypyrrolidine-2-carboxylic acid (163431-76-3) → (2S,3S,4S)-3-Methoxycarbonylmethyl-4-(2-methoxy-phenyl)-pyrrolidine-2-carboxylic acid methyl ester (126891-21-2)

Guidance literature:

Multi-step reaction with 16 steps

1: 1) tBuOCl, 2) Et₃N

2: pyridine

3: 70 percent / TBAF

4: 100 percent / N,N-dimethylaniline

5: 100 percent / nBu₃SnH, AIBN / benzene / Heating

6: DBU / toluene / Heating

7: Jones-oxidation

8: 94 percent / BH₃-Me₂S / tetrahydrofuran / 0 deg C to r.t.

9: 65 percent / Et₃N, DMAP

10: 86 percent / pyridine

11: H₂ / Pd/C

12: TBAF

14: PDC / dimethylformamide

16: H₂, KOH

With pyridine; dmap; potassium hydroxide; dipyridinium dichromate; 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; palladium on activated charcoal; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; benzene;

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

upstream raw materials:

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

methyl iodide

(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:

MFPA