(S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(1-ethoxy-buta-1,3-dienyl)-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole

Base Information

• Chemical Name: (S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(1-ethoxy-buta-1,3-dienyl)-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole
• CAS No.: 790661-80-2
• Molecular Formula: C₂₄H₃₇NO₄SSi
• Molecular Weight: 463.714

Synonyms:(S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(1-ethoxy-buta-1,3-dienyl)-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole

Chemical Property of (S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(1-ethoxy-buta-1,3-dienyl)-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole

Chemical Property:

Purity/Quality:

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Technology Process of (S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(1-ethoxy-buta-1,3-dienyl)-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole

There total 2 articles about (S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(1-ethoxy-buta-1,3-dienyl)-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole 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: 65.0%

(E)-2-[(1-ethoxy)buta-1,3-dienyl]-5,5-dimethyl-[1,3,2]dioxaborinane (426840-81-5) + (S)-trifluoromethanesulfonic acid 5-(tert-butyl-dimethylsilanyloxymethyl)-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl ester (790661-79-9) → (S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(1-ethoxy-buta-1,3-dienyl)-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole (790661-80-2)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In tetrahydrofuran; at 60 ℃; for 2h;

DOI:10.1021/jo0489263

Reference yield:

(S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-one → (S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(1-ethoxy-buta-1,3-dienyl)-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole (790661-80-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: KHMDS / tetrahydrofuran; toluene / 1.5 h / -78 °C

1.2: tetrahydrofuran; toluene / -78 - 0 °C

2.1: 65 percent / (Ph₃P)2PdCl₂; aq. Na₂CO₃ / tetrahydrofuran / 2 h / 60 °C

With bis-triphenylphosphine-palladium(II) chloride; potassium hexamethylsilazane; sodium carbonate; In tetrahydrofuran; toluene;

DOI:10.1021/jo0489263

Reference yield:

(S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(1-ethoxy-buta-1,3-dienyl)-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-pyrrole (790661-80-2) → (S)-1-[5-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-but-2-en-1-one (790661-81-3)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 6h;

DOI:10.1021/jo0489263

upstream raw materials:

(E)-2-[(1-ethoxy)buta-1,3-dienyl]-5,5-dimethyl-[1,3,2]dioxaborinane

(S)-trifluoromethanesulfonic acid 5-(tert-butyl-dimethylsilanyloxymethyl)-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl ester

Downstream raw materials:

(S)-1-[5-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrol-2-yl]-but-2-en-1-one

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