N-((1S,2R)-2-hydroxy-1-phenylpentyl)-4-methylbenzenesulfonamide

Base Information

• Chemical Name: N-((1S,2R)-2-hydroxy-1-phenylpentyl)-4-methylbenzenesulfonamide
• CAS No.: 1202798-64-8
• Molecular Formula: C₁₈H₂₃NO₃S
• Molecular Weight: 333.452
• Mol file: 1202798-64-8.mol

Synonyms:N-((1S,2R)-2-hydroxy-1-phenylpentyl)-4-methylbenzenesulfonamide

Chemical Property of N-((1S,2R)-2-hydroxy-1-phenylpentyl)-4-methylbenzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-((1S,2R)-2-hydroxy-1-phenylpentyl)-4-methylbenzenesulfonamide

There total 2 articles about N-((1S,2R)-2-hydroxy-1-phenylpentyl)-4-methylbenzenesulfonamide 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: 88.0%

tert-butyl (1S,2R)-2-hydroxy-1-phenylpentylcarbamate (1202798-61-5) + p-toluenesulfonyl chloride (98-59-9) → N-((1S,2R)-2-hydroxy-1-phenylpentyl)-4-methylbenzenesulfonamide (1202798-64-8)

Guidance literature:

tert-butyl (1S,2R)-2-hydroxy-1-phenylpentylcarbamate; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

p-toluenesulfonyl chloride; With triethylamine; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jo902244y

Reference yield:

N-(benzylidene)-p-methylbenzenesulfonamide (51608-60-7) + 2,2'-(butane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) → N-((1S,2R)-2-hydroxy-1-phenylpentyl)-4-methylbenzenesulfonamide (1202798-64-8) + N-(2-hydroxy-1-phenylpentyl)-4-methylbenzenesulfonamide

Guidance literature:

2,2'-(butane-1,1-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane); With C₂₄H₂₀NO₃P; copper(I) bromide; lithium tert-butoxide; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere; Glovebox;

N-(benzylidene)-p-methylbenzenesulfonamide; In tetrahydrofuran; at 50 ℃; for 24h; Sealed tube;

With dihydrogen peroxide; sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 3h; Overall yield = 67 %; Overall yield = 45 mg; stereoselective reaction;

DOI:10.1002/anie.201705829

Reference yield: 98.0%

N-((1S,2R)-2-hydroxy-1-phenylpentyl)-4-methylbenzenesulfonamide (1202798-64-8) → (2S,3S)-2-phenyl-3-propyl-1-tosylaziridine

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/jo902244y

upstream raw materials:

tert-butyl (1S,2R)-2-hydroxy-1-phenylpentylcarbamate

p-toluenesulfonyl chloride

N-(benzylidene)-p-methylbenzenesulfonamide