(1R,2'S,E)-{1-[(tert-butoxy)methyl]-2-[2'-(hydroxymethyl)cyclopentylidene]ethyl}[(2,4,6-trimethylphenyl)sulfonyl]amine

Base Information

• Chemical Name: (1R,2'S,E)-{1-[(tert-butoxy)methyl]-2-[2'-(hydroxymethyl)cyclopentylidene]ethyl}[(2,4,6-trimethylphenyl)sulfonyl]amine
• CAS No.: 462652-93-3
• Molecular Formula: C₂₂H₃₅NO₄S
• Molecular Weight: 409.59

Synonyms:(1R,2'S,E)-{1-[(tert-butoxy)methyl]-2-[2'-(hydroxymethyl)cyclopentylidene]ethyl}[(2,4,6-trimethylphenyl)sulfonyl]amine

Chemical Property of (1R,2'S,E)-{1-[(tert-butoxy)methyl]-2-[2'-(hydroxymethyl)cyclopentylidene]ethyl}[(2,4,6-trimethylphenyl)sulfonyl]amine

Chemical Property:

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Technology Process of (1R,2'S,E)-{1-[(tert-butoxy)methyl]-2-[2'-(hydroxymethyl)cyclopentylidene]ethyl}[(2,4,6-trimethylphenyl)sulfonyl]amine

There total 11 articles about (1R,2'S,E)-{1-[(tert-butoxy)methyl]-2-[2'-(hydroxymethyl)cyclopentylidene]ethyl}[(2,4,6-trimethylphenyl)sulfonyl]amine 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:

N-(1-tert-butoxymethyl-2-{2-[(isopropoxy-dimethyl-silanyl)-methyl]-cyclopentylidene}-ethyl)-2,4,6-trimethyl-benzenesulfonamide (462652-91-1) → (1R,2'S,E)-{1-[(tert-butoxy)methyl]-2-[2'-(hydroxymethyl)cyclopentylidene]ethyl}[(2,4,6-trimethylphenyl)sulfonyl]amine (462652-93-3)

Guidance literature:

With potassium fluoride; dihydrogen peroxide; In water; N,N-dimethyl-formamide; at 20 ℃; for 10h;

DOI:10.1021/jo025922u

Reference yield:

1-iodocyclopentene (17497-52-8) → (1R,2'S,E)-{1-[(tert-butoxy)methyl]-2-[2'-(hydroxymethyl)cyclopentylidene]ethyl}[(2,4,6-trimethylphenyl)sulfonyl]amine (462652-93-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: diisobutylaluminum hydride / CH₂Cl₂; toluene / 1 h / -78 °C

1.2: 0.9 g / BuLi; ZnCl₂; LiCl / tetrahydrofuran; hexane; CH₂Cl₂ / -78 - 20 °C

2.1: NaH / tetrahydrofuran / 0.5 h / Heating

2.2: 47 percent / tetrahydrofuran / 3 h / 20 °C

3.1: CuCN; LiCl / tetrahydrofuran / -78 - 0 °C

3.2: tetrahydrofuran / -78 - 0 °C

4.1: 126 mg / KF; H₂O₂ / H₂O / 10 h / 20 °C

5.1: TMSOTf; 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6.1: Et₃N / tetrahydrofuran

With 2,6-dimethylpyridine; potassium fluoride; trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; triethylamine; lithium chloride; In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1021/jo025922u

Reference yield:

methyl N-(tert-butoxycarbonyl)-O-(tert-butyl)-L-serinate (174363-87-2) → (1R,2'S,E)-{1-[(tert-butoxy)methyl]-2-[2'-(hydroxymethyl)cyclopentylidene]ethyl}[(2,4,6-trimethylphenyl)sulfonyl]amine (462652-93-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: diisobutylaluminum hydride / CH₂Cl₂; toluene / 1 h / -78 °C

1.2: 0.9 g / BuLi; ZnCl₂; LiCl / tetrahydrofuran; hexane; CH₂Cl₂ / -78 - 20 °C

2.1: NaH / tetrahydrofuran / 0.5 h / Heating

2.2: 47 percent / tetrahydrofuran / 3 h / 20 °C

3.1: CuCN; LiCl / tetrahydrofuran / -78 - 0 °C

3.2: tetrahydrofuran / -78 - 0 °C

4.1: 126 mg / KF; H₂O₂ / H₂O / 10 h / 20 °C

5.1: TMSOTf; 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6.1: Et₃N / tetrahydrofuran

With 2,6-dimethylpyridine; potassium fluoride; trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; triethylamine; lithium chloride; In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1021/jo025922u

upstream raw materials:

2-mesitylenesulphonyl chloride

N-(1-tert-butoxymethyl-2-{2-[(isopropoxy-dimethyl-silanyl)-methyl]-cyclopentylidene}-ethyl)-2,4,6-trimethyl-benzenesulfonamide

1-iodocyclopentene

methyl N-(tert-butoxycarbonyl)-O-(tert-butyl)-L-serinate

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