3-Pyrrolidinol, 2-[(4-methoxyphenyl)methyl]-1-(phenylmethyl)-, acetate (ester), (2R,3R)-

Base Information

• Chemical Name: 3-Pyrrolidinol, 2-[(4-methoxyphenyl)methyl]-1-(phenylmethyl)-, acetate (ester), (2R,3R)-
• CAS No.: 676449-20-0
• Molecular Formula: C21H25NO3
• Molecular Weight: 339.434
• Mol file: 676449-20-0.mol

Synonyms:

Chemical Property of 3-Pyrrolidinol, 2-[(4-methoxyphenyl)methyl]-1-(phenylmethyl)-, acetate (ester), (2R,3R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Pyrrolidinol, 2-[(4-methoxyphenyl)methyl]-1-(phenylmethyl)-, acetate (ester), (2R,3R)-

There total 6 articles about 3-Pyrrolidinol, 2-[(4-methoxyphenyl)methyl]-1-(phenylmethyl)-, acetate (ester), (2R,3R)- 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:

(R)-2-Dibenzylamino-3-(4-methoxy-phenyl)-propionic acid methyl ester (400009-34-9) → (2R,3R)-3-acetoxy-1-benzyl-2-(4-methoxybenzyl)pyrrolidine (676449-20-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 95 percent / aq. LiOH / tetrahydrofuran / 18 h / Heating

2.1: tetrahydrofuran / 2.5 h / 20 °C

3.1: lithium hexamethyldisilazide / tetrahydrofuran / 0.33 h / -78 °C

3.2: 1.76 g / tetrahydrofuran / 2 h / -78 °C

4.1: 83 percent / NaCNBH₃; AcOH / methanol; diethyl ether / 18 h / 20 °C / pH 4

5.1: 95 percent / LiAlH₄ / tetrahydrofuran / 6 h / -78 °C

6.1: DMAP; triisopropylbenzene sulfonyl chloride / CH₂Cl₂ / 18 h / 0 °C

6.2: 85 percent / Dowex Cl^(1-)

7.1: 80 percent / K₂CO₃; H₂ / Pd/C / methanol / 0.33 h / 20 °C / 760.05 Torr

8.1: 87 percent / triethylamine / CH₂Cl₂ / 18 h / 20 °C

With dmap; lithium hydroxide; lithium aluminium tetrahydride; triisopropylbenzene sulfonyl chloride; hydrogen; sodium cyanoborohydride; potassium carbonate; acetic acid; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 3.2: Claisen condensation;

DOI:10.1039/b311242j

Reference yield:

ethyl (3R,4R)-4-dibenzylamino-3-hydroxy-5-(4-methoxyphenyl)pentanoate (676449-17-5) → (2R,3R)-3-acetoxy-1-benzyl-2-(4-methoxybenzyl)pyrrolidine (676449-20-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 95 percent / LiAlH₄ / tetrahydrofuran / 6 h / -78 °C

2.1: DMAP; triisopropylbenzene sulfonyl chloride / CH₂Cl₂ / 18 h / 0 °C

2.2: 85 percent / Dowex Cl^(1-)

3.1: 80 percent / K₂CO₃; H₂ / Pd/C / methanol / 0.33 h / 20 °C / 760.05 Torr

4.1: 87 percent / triethylamine / CH₂Cl₂ / 18 h / 20 °C

With dmap; lithium aluminium tetrahydride; triisopropylbenzene sulfonyl chloride; hydrogen; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1039/b311242j

Reference yield:

ethyl (4R)-4-dibenzylamino-5-(4-methoxyphenyl)-3-oxopentanoate (676449-16-4) → (2R,3R)-3-acetoxy-1-benzyl-2-(4-methoxybenzyl)pyrrolidine (676449-20-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 83 percent / NaCNBH₃; AcOH / methanol; diethyl ether / 18 h / 20 °C / pH 4

2.1: 95 percent / LiAlH₄ / tetrahydrofuran / 6 h / -78 °C

3.1: DMAP; triisopropylbenzene sulfonyl chloride / CH₂Cl₂ / 18 h / 0 °C

3.2: 85 percent / Dowex Cl^(1-)

4.1: 80 percent / K₂CO₃; H₂ / Pd/C / methanol / 0.33 h / 20 °C / 760.05 Torr

5.1: 87 percent / triethylamine / CH₂Cl₂ / 18 h / 20 °C

With dmap; lithium aluminium tetrahydride; triisopropylbenzene sulfonyl chloride; hydrogen; sodium cyanoborohydride; potassium carbonate; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1039/b311242j

upstream raw materials:

(R)-2-Dibenzylamino-3-(4-methoxy-phenyl)-propionic acid methyl ester

(2R)-2-dibenzylamino-3-(methoxyphenyl)propanoic acid

(3R,4R)-4-dibenzylamino-3-hydroxy-5-(4-methoxyphenyl)pentan-1-ol

ethyl (3R,4R)-4-dibenzylamino-3-hydroxy-5-(4-methoxyphenyl)pentanoate