(R)-(+)-N-[1-(benzo[b]thiophen-2-yl)ethyl]-O-benzylhydroxylamine

Base Information

• Chemical Name: (R)-(+)-N-[1-(benzo[b]thiophen-2-yl)ethyl]-O-benzylhydroxylamine
• CAS No.: 142606-23-3
• Molecular Formula: C₁₇H₁₇NOS
• Molecular Weight: 283.394
• Mol file: 142606-23-3.mol

Synonyms:(R)-(+)-N-[1-(benzo[b]thiophen-2-yl)ethyl]-O-benzylhydroxylamine

Chemical Property of (R)-(+)-N-[1-(benzo[b]thiophen-2-yl)ethyl]-O-benzylhydroxylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(+)-N-[1-(benzo[b]thiophen-2-yl)ethyl]-O-benzylhydroxylamine

There total 6 articles about (R)-(+)-N-[1-(benzo[b]thiophen-2-yl)ethyl]-O-benzylhydroxylamine 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: 86.0%

(2-mercaptophenyl)methyl-triphenylphosphonium bromide (116849-93-5) + (R)-3-Benzyloxy-4-methyl-oxazolidine-2,5-dione (142696-73-9) → (R)-(+)-N-[1-(benzo[b]thiophen-2-yl)ethyl]-O-benzylhydroxylamine (142606-23-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; for 12h; Ambient temperature;

DOI:10.1016/S0040-4039(00)79043-5

Reference yield:

1-(benzo[b]thiophen-2-yl)ethanone oxime O-benzyl ether → (S)-(-)-N-[1-(benzo[b]thiophen-2-yl)ethyl]-O-benzylhydroxylamine + (R)-(+)-N-[1-(benzo[b]thiophen-2-yl)ethyl]-O-benzylhydroxylamine (142606-23-3)

Guidance literature:

1-(benzo[b]thiophen-2-yl)ethanone oxime O-benzyl ether; With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 40h;

With hydrogenchloride; In tetrahydrofuran; at 0 - 20 ℃; for 18h; Further stages. Title compound not separated from byproducts.;

DOI:10.1016/j.tetasy.2008.03.026

Reference yield:

N-benzyloxyamine (622-33-3) → (R)-(+)-N-[1-(benzo[b]thiophen-2-yl)ethyl]-O-benzylhydroxylamine (142606-23-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) Tf₂O, 2,6-lutidine / 1) CH₂Cl₂, 0 deg C, 5 min, 2) CH₂Cl₂, r.t., 18 h

2: 99 percent / trifluoroacetic acid / CH₂Cl₂ / 3 h / Ambient temperature

3: toluene; tetrahydrofuran / 2 h / 45 °C

4: hexane; tetrahydrofuran / 3 h / Heating

5: 86 percent / NaH / tetrahydrofuran; dimethylformamide / 12 h / Ambient temperature

With 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)79043-5

upstream raw materials:

(2-mercaptophenyl)methyl-triphenylphosphonium bromide

(R)-3-Benzyloxy-4-methyl-oxazolidine-2,5-dione

N-benzyloxyamine

N-Benzyloxy-D-Alanin

Downstream raw materials:

(R)-(-)-N-[1-(benzo[b]thiophen-2-yl)ethyl]-N-benzyloxy-urea