[1R-(1α,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl-1-N-methyl-N-methoxy cyclopropanecarboxamide

Base Information

• Chemical Name: [1R-(1α,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl-1-N-methyl-N-methoxy cyclopropanecarboxamide
• CAS No.: 443149-81-3
• Molecular Formula: C₂₃H₃₉NO₄Si
• Molecular Weight: 421.652

Synonyms:[1R-(1α,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl-1-N-methyl-N-methoxy cyclopropanecarboxamide

Chemical Property of [1R-(1α,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl-1-N-methyl-N-methoxy cyclopropanecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [1R-(1α,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl-1-N-methyl-N-methoxy cyclopropanecarboxamide

There total 3 articles about [1R-(1α,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl-1-N-methyl-N-methoxy cyclopropanecarboxamide 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:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + 3-(4-methoxyphenyl)-(2Z)-propenyl diazoacetate (443149-79-9) → [1R-(1α,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl-1-N-methyl-N-methoxy cyclopropanecarboxamide (443149-81-3) + [1S-(1α,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl-1-N-methyl-N-methoxy cyclopropanecarboxamide

Guidance literature:

3-(4-methoxyphenyl)-(2Z)-propenyl diazoacetate; Rh₂[(2S)-5-hydroxypyrrolidine-2-COOMe]4; In dichloromethane; for 18h; Heating;

N,O-dimethylhydroxylamine*hydrochloride; With trimethylaluminum; In hexane; dichloromethane; at 20 ℃;

triisopropylsilyl trifluoromethanesulfonate; With 2,6-dimethylpyridine; In dichloromethane; water; at 0 ℃; for 2h; Further stages. Title compound not separated from byproducts.;

DOI:10.1021/jo0110698

Reference yield:

4-(4-methoxyphenyl)prop-2-yn-1-ol (37614-59-8) → [1R-(1α,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl-1-N-methyl-N-methoxy cyclopropanecarboxamide (443149-81-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 84 percent / NaOH; H₂; ethylenediamine / Ni(OAc)2*4H₂O; NaBH₄ / ethanol / 72 h / 760.05 Torr

2.1: N,N-dimethylaniline / CH₂Cl₂ / 0.17 h / 0 °C

2.2: 65 percent / triethylamine / CH₂Cl₂ / 20 °C

3.1: Rh₂[5(S)-MEPY]4 / CH₂Cl₂ / 18 h / Heating

3.2: Me₃Al / hexane; CH₂Cl₂ / 20 °C

3.3: 2,6-lutidine / CH₂Cl₂; H₂O / 2 h / 0 °C

With sodium hydroxide; hydrogen; N,N-dimethyl-aniline; ethylenediamine; sodium tetrahydroborate; Rh₂[(2S)-5-hydroxypyrrolidine-2-COOMe]4; nickel diacetate; In ethanol; dichloromethane; 2.2: Corey-Myers reaction / 3.2: Weinreb reaction;

DOI:10.1021/jo0110698

Reference yield:

(Z)-3-(4-methoxyphenyl)prop-2-en-1-ol (173542-65-9) → [1R-(1α,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl-1-N-methyl-N-methoxy cyclopropanecarboxamide (443149-81-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N,N-dimethylaniline / CH₂Cl₂ / 0.17 h / 0 °C

1.2: 65 percent / triethylamine / CH₂Cl₂ / 20 °C

2.1: Rh₂[5(S)-MEPY]4 / CH₂Cl₂ / 18 h / Heating

2.2: Me₃Al / hexane; CH₂Cl₂ / 20 °C

2.3: 2,6-lutidine / CH₂Cl₂; H₂O / 2 h / 0 °C

With N,N-dimethyl-aniline; Rh₂[(2S)-5-hydroxypyrrolidine-2-COOMe]4; In dichloromethane; 1.2: Corey-Myers reaction / 2.2: Weinreb reaction;

DOI:10.1021/jo0110698

upstream raw materials:

triisopropylsilyl trifluoromethanesulfonate

N,O-dimethylhydroxylamine*hydrochloride

3-(4-methoxyphenyl)-(2Z)-propenyl diazoacetate

4-(4-methoxyphenyl)prop-2-yn-1-ol

Downstream raw materials:

[1S-(1β,2α,3α)]-2-(4-methoxyphenyl)-3-triisopropylsilyloxymethyl cyclopropane-1-carboxylic acid

[1S-(1α,2β,3α)]-2-(3-(R)-isobutylsuccinimido)-3-(4-methoxyphenyl)cyclopropane carboxaldehyde

[1S-(1α,2β,3β)]-1-(3-(R)-isobutylsuccinimido)-2-hydroxymethyl-3-(4-methoxyphenyl)cyclopropane

[1S-(1α,2β,3α)]-2-(3-(R)-isobutylsuccinimido)-3-(4-methoxyphenyl)cyclopropanecarboxylic acid

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