[(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-(4-methoxy-phenyl)-methanol

Base Information

• Chemical Name: [(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-(4-methoxy-phenyl)-methanol
• CAS No.: 646039-38-5
• Molecular Formula: C₂₅H₃₇NO₅SSi
• Molecular Weight: 491.724
• Mol file: 646039-38-5.mol

Synonyms:[(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-(4-methoxy-phenyl)-methanol

Chemical Property of [(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-(4-methoxy-phenyl)-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-(4-methoxy-phenyl)-methanol

There total 3 articles about [(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-(4-methoxy-phenyl)-methanol 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:

1-bromo-4-methoxy-benzene (104-92-7) + (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carbaldehyde (863396-18-3) → [(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-(4-methoxy-phenyl)-methanol (646039-38-5)

Guidance literature:

1-bromo-4-methoxy-benzene; With magnesium;

(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carbaldehyde; In tetrahydrofuran; at 0 ℃; for 3h; Further stages.;

DOI:10.1016/j.tet.2007.05.059

Reference yield:

(2S,4R)-1-(4-methylphenyl)sulfonyl-2-hydroxymethyl-4-(t-butyldimethylsilanyloxy)pyrrolidine (261157-02-2) → [(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-(4-methoxy-phenyl)-methanol (646039-38-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (COCl)2; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

2.1: Mg

2.2: 8.67 g / tetrahydrofuran / 3 h / 0 °C

With oxalyl dichloride; magnesium; dimethyl sulfoxide; triethylamine; In dichloromethane; 1.1: Swern oxidation;

DOI:10.1016/j.tet.2007.05.059

Reference yield:

4-methoxyphenyl magnesium bromide (13139-86-1) + (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carbaldehyde (863396-18-3) → [(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-(4-methoxy-phenyl)-methanol (646039-38-5)

Guidance literature:

In tetrahydrofuran; at -78 - 0 ℃;

DOI:10.1055/s-2003-42102

upstream raw materials:

4-methoxyphenyl magnesium bromide

(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-pyrrolidine-2-carbaldehyde

1-bromo-4-methoxy-benzene

(2S,4R)-1-(4-methylphenyl)sulfonyl-2-hydroxymethyl-4-(t-butyldimethylsilanyloxy)pyrrolidine

Downstream raw materials:

(1R,4S)-1-methyl-8-methoxy-3-(4-toluenesulfonyl)-2,3,4,5-tetrahydro-1,4-methano-3-benzazepine

(2R,4S)-4-hydroxy-2-(4-methoxybenzyl)-4-methyl-1-(4-toluenesulfonyl)pyrrolidine

(R)-5-(4-Methoxy-benzyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-one

(3R,5R)-5-(4-Methoxy-benzyl)-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol