rel-(3R,3aS,7aR)-2-benzyl-3-ethoxy-2,3,3a,4,7,7a-hexahydro-7a-<5-(trimethylsilyl)-3-pentenyl>-1-isoindolone

Base Information

• Chemical Name: rel-(3R,3aS,7aR)-2-benzyl-3-ethoxy-2,3,3a,4,7,7a-hexahydro-7a-<5-(trimethylsilyl)-3-pentenyl>-1-isoindolone
• CAS No.: 121823-64-1
• Molecular Formula: C₂₅H₃₇NO₂Si
• Molecular Weight: 411.66

Synonyms:rel-(3R,3aS,7aR)-2-benzyl-3-ethoxy-2,3,3a,4,7,7a-hexahydro-7a-<5-(trimethylsilyl)-3-pentenyl>-1-isoindolone

Chemical Property of rel-(3R,3aS,7aR)-2-benzyl-3-ethoxy-2,3,3a,4,7,7a-hexahydro-7a-<5-(trimethylsilyl)-3-pentenyl>-1-isoindolone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of rel-(3R,3aS,7aR)-2-benzyl-3-ethoxy-2,3,3a,4,7,7a-hexahydro-7a-<5-(trimethylsilyl)-3-pentenyl>-1-isoindolone

There total 3 articles about rel-(3R,3aS,7aR)-2-benzyl-3-ethoxy-2,3,3a,4,7,7a-hexahydro-7a-<5-(trimethylsilyl)-3-pentenyl>-1-isoindolone 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: 94.0%

rel-(3R,3aS,7aR)-2-benzyl-3-ethoxy-2,3,3a,4,7,7a-hexahydro-7a-<5-(trimethylsilyl)-3-pentynyl>-1-isoindolone (95455-17-7) → rel-(3R,3aS,7aR)-2-benzyl-3-ethoxy-2,3,3a,4,7,7a-hexahydro-7a-<5-(trimethylsilyl)-3-pentenyl>-1-isoindolone (121823-64-1)

Guidance literature:

With sodium hydroxide; sodium tetrahydroborate; hydrogen; nickel diacetate; ethylenediamine; In ethanol; for 17h;

DOI:10.1016/S0040-4020(01)90113-9

Reference yield:

5-iodo-1-(trimethylsilyl)-2-pentyne (88996-00-3) → rel-(3R,3aS,7aR)-2-benzyl-3-ethoxy-2,3,3a,4,7,7a-hexahydro-7a-<5-(trimethylsilyl)-3-pentenyl>-1-isoindolone (121823-64-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min., 2.) THF, -78 to 20 deg C

2: 94 percent / H₂, NaBH₄, Ni(OAc)2*4H₂O, 0.1M NaOH, 1,2-diaminoethane / ethanol / 17 h

With sodium hydroxide; sodium tetrahydroborate; hydrogen; nickel diacetate; ethylenediamine; lithium diisopropyl amide; In ethanol;

DOI:10.1016/S0040-4020(01)90113-9

Reference yield:

2-Benzyl-3-ethoxy-2,3,3a,4,7,7a-hexahydro-isoindol-1-one (95455-15-5) → rel-(3R,3aS,7aR)-2-benzyl-3-ethoxy-2,3,3a,4,7,7a-hexahydro-7a-<5-(trimethylsilyl)-3-pentenyl>-1-isoindolone (121823-64-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 30 min., 2.) THF, -78 to 20 deg C

2: 94 percent / H₂, NaBH₄, Ni(OAc)2*4H₂O, 0.1M NaOH, 1,2-diaminoethane / ethanol / 17 h

With sodium hydroxide; sodium tetrahydroborate; hydrogen; nickel diacetate; ethylenediamine; lithium diisopropyl amide; In ethanol;

DOI:10.1016/S0040-4020(01)90113-9

upstream raw materials:

rel-(3R,3aS,7aR)-2-benzyl-3-ethoxy-2,3,3a,4,7,7a-hexahydro-7a-<5-(trimethylsilyl)-3-pentynyl>-1-isoindolone

5-iodo-1-(trimethylsilyl)-2-pentyne

2-Benzyl-3-ethoxy-2,3,3a,4,7,7a-hexahydro-isoindol-1-one

Downstream raw materials:

rel-(1R,2S)-11-benzyl-10-vinyl-11-azatricyclo<5.3.2.0^2,7>-4-dodecen-12-one

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