2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxymethyl-3-(4-octyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxymethyl-3-(4-octyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 928653-29-6
• Molecular Formula: C₄₃H₆₃NO₅Si
• Molecular Weight: 702.062

Synonyms:2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxymethyl-3-(4-octyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property of 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxymethyl-3-(4-octyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxymethyl-3-(4-octyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 12 articles about 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxymethyl-3-(4-octyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 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: 100.0%

2-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxymethyl-3-(4-octyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (928653-24-1) + chloromethyl methyl ether (107-30-2) → 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxymethyl-3-(4-octyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (928653-29-6)

Guidance literature:

With dmap; N,N-diethyl-N-isopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1016/j.bmcl.2006.10.014

Reference yield:

((E)-2-Oct-1-enyl)-benzo[1,3,2]dioxaborole (147024-83-7) → 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxymethyl-3-(4-octyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (928653-29-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Pd(Ph₃P)4; NaHCO₃ / 1,2-dimethoxy-ethane / Heating

2.1: 100 percent / H₂ / Pd/C / ethyl acetate / 20 °C

3.1: Super-Hydride / tetrahydrofuran / -78 °C

3.2: PPTS / tetrahydrofuran / -78 - 20 °C

4.1: TiCl₄ / CH₂Cl₂ / -78 - 0 °C

5.1: 69 percent / Grubbs 2nd gen. cat.; N-allyltritylamine; iPr₂NEt / toluene / Heating

6.1: O₃ / CH₂Cl₂; methanol / -78 °C

6.2: Me₂S / CH₂Cl₂; methanol

7.1: NaBH₄ / methanol / 0 °C

8.1: 100 percent / i-PrNEt₂; DMAP / CH₂Cl₂ / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N,N-diethyl-N-isopropylamine; N-tritylprop-2-en-1-amine; hydrogen; titanium tetrachloride; lithium triethylborohydride; sodium hydrogencarbonate; ozone; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; ethyl acetate; toluene; 1.1: Suzuki coupling;

DOI:10.1016/j.bmcl.2006.10.014

Reference yield:

tert-butyl (2S,3R)-3-(4-bromophenyl)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-oxopyrrolidine-1-carboxylate (928653-20-7) → 2-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxymethyl-3-(4-octyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (928653-29-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Pd(Ph₃P)4; NaHCO₃ / 1,2-dimethoxy-ethane / Heating

2.1: 100 percent / H₂ / Pd/C / ethyl acetate / 20 °C

3.1: Super-Hydride / tetrahydrofuran / -78 °C

3.2: PPTS / tetrahydrofuran / -78 - 20 °C

4.1: TiCl₄ / CH₂Cl₂ / -78 - 0 °C

5.1: 69 percent / Grubbs 2nd gen. cat.; N-allyltritylamine; iPr₂NEt / toluene / Heating

6.1: O₃ / CH₂Cl₂; methanol / -78 °C

6.2: Me₂S / CH₂Cl₂; methanol

7.1: NaBH₄ / methanol / 0 °C

8.1: 100 percent / i-PrNEt₂; DMAP / CH₂Cl₂ / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N,N-diethyl-N-isopropylamine; N-tritylprop-2-en-1-amine; hydrogen; titanium tetrachloride; lithium triethylborohydride; sodium hydrogencarbonate; ozone; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; ethyl acetate; toluene; 1.1: Suzuki coupling;

DOI:10.1016/j.bmcl.2006.10.014

upstream raw materials:

2-(tert-butyl-diphenyl-silanyloxymethyl)-5-hydroxymethyl-3-(4-octyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

chloromethyl methyl ether

((E)-2-Oct-1-enyl)-benzo[1,3,2]dioxaborole

tert-butyl (2S,3R)-3-(4-bromophenyl)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-oxopyrrolidine-1-carboxylate

Downstream raw materials:

(2S,3R,5R)-2-Hydroxymethyl-5-methoxymethoxymethyl-3-(4-octyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

2-(di-tert-butoxy-phosphoryloxymethyl)-5-methoxymethoxymethyl-3-(4-octyl-phenyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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