(alphaS,3R,4R)-4-(3-Hydroxyphenyl)-3,4-dimethyl-alpha-(phenylmethyl)-1-piperidinepropanoic acid methyl ester

Base Information

• Chemical Name: (alphaS,3R,4R)-4-(3-Hydroxyphenyl)-3,4-dimethyl-alpha-(phenylmethyl)-1-piperidinepropanoic acid methyl ester
• CAS No.: 170098-29-0
• Molecular Formula: C24H31NO3
• Molecular Weight: 381.515
• Mol file: 170098-29-0.mol

Synonyms:Poldine metilsulfate;(S)-2-benziloyloxymethyl-1,1-dimethyl-pyrrolidinium,methyl sulfate;Poldine methylsulfate (USAN);Poldini metilsulfas;Poldoni methylsulfas;(S)-2-Benziloyloxymethyl-1,1-dimethyl-pyrrolidinium,Methylsulfat;(S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propionic acid methyl ester;Metilsulfato de poldina;Poldine methylsulphate;Metilsulfate de poldine;Poldine methylsulfate;查看更多英文别名收起

Chemical Property of (alphaS,3R,4R)-4-(3-Hydroxyphenyl)-3,4-dimethyl-alpha-(phenylmethyl)-1-piperidinepropanoic acid methyl ester

Chemical Property:

• Boiling Point: 520℃
• PKA: 9.96±0.10(Predicted)
• Flash Point: 268℃
• PSA: 49.77000
• Density: 1.089
• LogP: 3.96150

Purity/Quality:

99.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (alphaS,3R,4R)-4-(3-Hydroxyphenyl)-3,4-dimethyl-alpha-(phenylmethyl)-1-piperidinepropanoic acid methyl ester

There total 14 articles about (alphaS,3R,4R)-4-(3-Hydroxyphenyl)-3,4-dimethyl-alpha-(phenylmethyl)-1-piperidinepropanoic 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: 33.0%

benzyl bromide (100-39-0) + methyl (3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinepropanoate (170098-39-2) → methyl (αS,3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-α-(phenylmethyl)-1-piperidinepropanoate (170098-29-0) + methyl (αS,3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-α-(phenylmethyl)-1-piperidinepropanoate

Guidance literature:

benzyl bromide; methyl (3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinepropanoate; With lithium diisopropyl amide; at -35 - -30 ℃;

With hydrogenchloride; In methanol; at 0 - 5 ℃; for 2h;

DOI:10.13005/ojc/340246

Reference yield:

benzyl bromide (100-39-0) + methyl (3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinepropanoate (170098-39-2) → methyl (αS,3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-α-(phenylmethyl)-1-piperidinepropanoate (170098-29-0)

Guidance literature:

methyl (3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinepropanoate; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; n-heptane; at -25 - 30 ℃; for 2.5 - 5h;

benzyl bromide; In tetrahydrofuran; hexane; n-heptane; at -25 - -20 ℃; for 18h;

Reference yield:

3-[(3R,4R)-3,4-dimethylpiperidin-4-yl]phenol (119193-19-0) → methyl (αS,3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-α-(phenylmethyl)-1-piperidinepropanoate (170098-29-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / tetrahydrofuran / 4 h / 45 °C

2: 1.) LDA / 1.) THF, -30 deg C, 15 min, 2.) -15 - -20 deg C, 3 h

With lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo951403y

upstream raw materials:

benzyl bromide

methyl (3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinepropanoate

3-[(3R,4R)-3,4-dimethylpiperidin-4-yl]phenol

(3R,4R)-3,4-dimethyl-4-<3-(1-methylethoxy)phenyl>piperidinecarboxylic acid phenyl ester

Downstream raw materials:

(S)-methyl 2-benzyl-3-((3R,4R)-3,4-dimethyl-4-(3-(trifluoromethyl-sulfonyloxy)phenyl)piperidin-1-yl)propanoate

ADL 08-0011

(+)-<<2'(S)-<<4(R)-3-(hydroxyphenyl)-3(R),4-dimethyl-1-piperidinyl>methyl>-1-oxo-3-phenylpropyl>amino>acetic acid 2-methylpropyl ester

Entereg