(5S)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(methoxycarbonyl)-2-pyrrolidinone

Base Information

• Chemical Name: (5S)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(methoxycarbonyl)-2-pyrrolidinone
• CAS No.: 245674-31-1
• Molecular Formula: C₂₃H₂₉NO₄Si
• Molecular Weight: 411.573
• Mol file: 245674-31-1.mol

Synonyms:(5S)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(methoxycarbonyl)-2-pyrrolidinone

Chemical Property of (5S)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(methoxycarbonyl)-2-pyrrolidinone

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (5S)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(methoxycarbonyl)-2-pyrrolidinone

There total 1 articles about (5S)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(methoxycarbonyl)-2-pyrrolidinone 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: 86.0%

(5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one (132974-83-5) + methyl chloroformate (79-22-1) → (5S)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(methoxycarbonyl)-2-pyrrolidinone (245674-31-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1021/jo9903297

Reference yield: 93.0%

(5S)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(methoxycarbonyl)-2-pyrrolidinone (245674-31-1) → (5S)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(methoxycarbonyl)-2-hydroxypyrrolidine

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

DOI:10.1021/jo9903297

Reference yield:

(5S)-5-[(tert-butyldiphenylsilyloxy)methyl]-1-(methoxycarbonyl)-2-pyrrolidinone (245674-31-1) → (2S)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-(methoxycarbonyl)-4-pyrroline (223595-44-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 93 percent / DIBAL-H / tetrahydrofuran; hexane / 1 h / -78 °C

2.1: (CF₃CO)2O; 2,6-lutidine / toluene / 7 h / 0 °C

2.2: 95 percent / 0.33 h / Heating

With 2,6-dimethylpyridine; diisobutylaluminium hydride; trifluoroacetic anhydride; In tetrahydrofuran; hexane; toluene; 1.1: Reduction / 2.1: Acylation / 2.2: Elimination;

DOI:10.1021/jo9903297

upstream raw materials:

(5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one

methyl chloroformate

Downstream raw materials:

(2S)-2-[(tert-butyldiphenylsilyloxy)methyl]-1-(methoxycarbonyl)-4-pyrroline