(3S,3aR,6R,6aS)-3-hydroxy-2-[(1R)-phenylethyl]-6-(trimethylsilyl)-3,3a,6,6a-tetrahydrocyclopenta[c]pyrrol-1(2H)-one

Base Information

• Chemical Name: (3S,3aR,6R,6aS)-3-hydroxy-2-[(1R)-phenylethyl]-6-(trimethylsilyl)-3,3a,6,6a-tetrahydrocyclopenta[c]pyrrol-1(2H)-one
• CAS No.: 1383844-06-1
• Molecular Formula: C₁₈H₂₅NO₂Si
• Molecular Weight: 315.488

Synonyms:(3S,3aR,6R,6aS)-3-hydroxy-2-[(1R)-phenylethyl]-6-(trimethylsilyl)-3,3a,6,6a-tetrahydrocyclopenta[c]pyrrol-1(2H)-one

Chemical Property of (3S,3aR,6R,6aS)-3-hydroxy-2-[(1R)-phenylethyl]-6-(trimethylsilyl)-3,3a,6,6a-tetrahydrocyclopenta[c]pyrrol-1(2H)-one

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Technology Process of (3S,3aR,6R,6aS)-3-hydroxy-2-[(1R)-phenylethyl]-6-(trimethylsilyl)-3,3a,6,6a-tetrahydrocyclopenta[c]pyrrol-1(2H)-one

There total 2 articles about (3S,3aR,6R,6aS)-3-hydroxy-2-[(1R)-phenylethyl]-6-(trimethylsilyl)-3,3a,6,6a-tetrahydrocyclopenta[c]pyrrol-1(2H)-one 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: 47.0%

2-(dichloromethyl)-N-[(1R)-1-phenylethyl]-5-(trimethylsilyl)-cyclopent-3-ene-1-carboxamide → (3S,3aR,6R,6aS)-3-hydroxy-2-[(1R)-phenylethyl]-6-(trimethylsilyl)-3,3a,6,6a-tetrahydrocyclopenta[c]pyrrol-1(2H)-one (1383844-06-1) + (3R,3aS,6S,6aR)-3-hydroxy-2-[(1R)-phenylethyl]-6-(trimethylsilyl)-3,3a,6,6a-tetrahydrocyclopenta[c]pyrrol-1(2H)-one (1383844-07-2)

Guidance literature:

With water; sodium hydrogencarbonate; In acetonitrile; for 7.5h; Reflux;

DOI:10.1016/j.tet.2012.05.036

Reference yield:

trimethylsilylcyclopentadiene (3559-74-8) → (3S,3aR,6R,6aS)-3-hydroxy-2-[(1R)-phenylethyl]-6-(trimethylsilyl)-3,3a,6,6a-tetrahydrocyclopenta[c]pyrrol-1(2H)-one (1383844-06-1)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / hexane / 4.5 h / 0 °C

2: benzene / 4 h / 20 °C / Inert atmosphere

3: water; sodium hydrogencarbonate / acetonitrile / 7.5 h / Reflux

With water; sodium hydrogencarbonate; triethylamine; In hexane; acetonitrile; benzene;

DOI:10.1016/j.tet.2012.05.036

Reference yield: 92.0%

(3S,3aR,6R,6aS)-3-hydroxy-2-[(1R)-phenylethyl]-6-(trimethylsilyl)-3,3a,6,6a-tetrahydrocyclopenta[c]pyrrol-1(2H)-one (1383844-06-1) → (1S,2R,5R)-2-(hydroxymethyl)-N-[(1R)-1-phenylethyl]-5-(trimethylsilyl)-cyclopent-3-ene-1-carboxamide (1383844-08-3)

Guidance literature:

With sodium tetrahydroborate; In 1,4-dioxane; water; for 5h; Reflux;

DOI:10.1016/j.tet.2012.05.036

upstream raw materials:

trimethylsilylcyclopentadiene

Downstream raw materials:

(1S,2R,5R)-2-(hydroxymethyl)-N-[(1R)-1-phenylethyl]-5-(trimethylsilyl)-cyclopent-3-ene-1-carboxamide

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