(1R,2R)-N-(3-hydroxy-2-methyl-1-phenyl-propyl)-4-methyl-benzenesulfonamide

Base Information

• Chemical Name: (1R,2R)-N-(3-hydroxy-2-methyl-1-phenyl-propyl)-4-methyl-benzenesulfonamide
• CAS No.: 127598-01-0
• Molecular Formula: C₁₇H₂₁NO₃S
• Molecular Weight: 319.425
• Mol file: 127598-01-0.mol

Synonyms:(1R,2R)-N-(3-hydroxy-2-methyl-1-phenyl-propyl)-4-methyl-benzenesulfonamide

Chemical Property of (1R,2R)-N-(3-hydroxy-2-methyl-1-phenyl-propyl)-4-methyl-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-N-(3-hydroxy-2-methyl-1-phenyl-propyl)-4-methyl-benzenesulfonamide

There total 16 articles about (1R,2R)-N-(3-hydroxy-2-methyl-1-phenyl-propyl)-4-methyl-benzenesulfonamide 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: 91.0%

(2R,3R)-2-methyl-3-phenyl-3-(toluene-4-sulfonylamino)-propionic acid methyl ester (904670-33-3) → (1R,2R)-N-(3-hydroxy-2-methyl-1-phenyl-propyl)-4-methyl-benzenesulfonamide (127598-01-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 2.5h;

DOI:10.1002/adsc.200505230

Reference yield: 82.0%

((2S*,3R*)-2-methyl-3-phenyl-1-tosylaziridin-2-yl)methanol → N-((1S*,2S*)-3-hydroxy-2-methyl-1-phenylpropyl)-4-methylbenzenesulfonamide (127598-01-0,127598-09-8)

Guidance literature:

With phenylsilane; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 16h; regioselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1002/anie.201808034

Reference yield:

N-(2-oxo-1-phenyl-propyl)-4-methyl-benzenosulfonamide (3893-40-1) → N-((R)-3-Hydroxy-2-methyl-1-phenyl-propyl)-4-methyl-benzenesulfonamide (127598-01-0,127598-09-8)

Guidance literature:

Multi-step reaction with 2 steps

1: Zn / TiCl₄ / tetrahydrofuran / 20 °C

2: 1.) catecholborane 2.) H₂O₂/NaOH / 1.) 2*4PPh₃ / 1.) 25 deg C, 36h

With sodium hydroxide; dihydrogen peroxide; zinc; benzo[1,3,2]dioxaborole; chloro(1,5-cyclooctadiene)rhodium(I) dimer; titanium tetrachloride; triphenylphosphine; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)93489-6

upstream raw materials:

4-methyl-N-(2-methyl-1-phenylallyl)benzenesulfonamide

N-(2-oxo-1-phenyl-propyl)-4-methyl-benzenosulfonamide

methyllithium

2-methyl-3-phenylprop-2-en-1-ol

Downstream raw materials:

(2R,3R)-(+)-2-methyl-3-(4-methylphenylsulfonamido)-3-phenylpropanoic acid