(-)-(8R,8aS)-5-(2-benzyloxyethyl)-8-methyl-6-(p-toluenesulfonyl)-Δ^5,6-indolizidine

Base Information

• Chemical Name: (-)-(8R,8aS)-5-(2-benzyloxyethyl)-8-methyl-6-(p-toluenesulfonyl)-Δ^5,6-indolizidine
• CAS No.: 288372-93-0
• Molecular Formula: C₂₅H₃₁NO₃S
• Molecular Weight: 425.592

Synonyms:(-)-(8R,8aS)-5-(2-benzyloxyethyl)-8-methyl-6-(p-toluenesulfonyl)-Δ^5,6-indolizidine

Chemical Property of (-)-(8R,8aS)-5-(2-benzyloxyethyl)-8-methyl-6-(p-toluenesulfonyl)-Δ^5,6-indolizidine

Chemical Property:

Purity/Quality:

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Technology Process of (-)-(8R,8aS)-5-(2-benzyloxyethyl)-8-methyl-6-(p-toluenesulfonyl)-Δ^5,6-indolizidine

There total 10 articles about (-)-(8R,8aS)-5-(2-benzyloxyethyl)-8-methyl-6-(p-toluenesulfonyl)-Δ^5,6-indolizidine 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:

(S)-1-{3-Benzyloxy-1-[1-(toluene-4-sulfonyl)-meth-(E)-ylidene]-propyl}-2-((S)-2-chloro-1-methyl-ethyl)-pyrrolidine → (-)-(8R,8aS)-5-(2-benzyloxyethyl)-8-methyl-6-(p-toluenesulfonyl)-Δ5,6-indolizidine (288372-93-0)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/jo000080p

Reference yield:

(S)-2-[(S)-1-((R)-1-Phenyl-ethyl)-pyrrolidin-2-yl]-propionic acid ethyl ester (212118-70-2) → (-)-(8R,8aS)-5-(2-benzyloxyethyl)-8-methyl-6-(p-toluenesulfonyl)-Δ5,6-indolizidine (288372-93-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 4.944 g / LiAlH₄ / diethyl ether / 1 h / 20 °C

2: 2.52 g / H₂ / 10percent Pd-C / ethanol / 144 h / 20 °C / 760.05 Torr

3: 70 percent / HCl; SOCl₂ / CHCl₃ / 3 h / Heating

4: KOH / H₂O

5: CH₂Cl₂ / 21 h / 20 °C

6: LDA / tetrahydrofuran / -78 °C

With hydrogenchloride; potassium hydroxide; lithium aluminium tetrahydride; thionyl chloride; hydrogen; lithium diisopropyl amide; 10percent Pd-C; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; chloroform; water; 1: Reduction / 2: dealkylation / 3: Chlorination / 4: exchange / 5: Addition / 6: Cyclization;

DOI:10.1021/jo000080p

Reference yield:

(S)-2-[(S)-1-((R)-1-Phenyl-ethyl)-pyrrolidin-2-yl]-propan-1-ol (288373-07-9) → (-)-(8R,8aS)-5-(2-benzyloxyethyl)-8-methyl-6-(p-toluenesulfonyl)-Δ5,6-indolizidine (288372-93-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 2.52 g / H₂ / 10percent Pd-C / ethanol / 144 h / 20 °C / 760.05 Torr

2: 70 percent / HCl; SOCl₂ / CHCl₃ / 3 h / Heating

3: KOH / H₂O

4: CH₂Cl₂ / 21 h / 20 °C

5: LDA / tetrahydrofuran / -78 °C

With hydrogenchloride; potassium hydroxide; thionyl chloride; hydrogen; lithium diisopropyl amide; 10percent Pd-C; In tetrahydrofuran; ethanol; dichloromethane; chloroform; water; 1: dealkylation / 2: Chlorination / 3: exchange / 4: Addition / 5: Cyclization;

DOI:10.1021/jo000080p

upstream raw materials:

((but-3-yn-1-yloxy)methyl)benzene

benzyl bromide

(S)-2-[(S)-1-((R)-1-Phenyl-ethyl)-pyrrolidin-2-yl]-propionic acid ethyl ester

(S)-(S)-2-Pyrrolidin-2-yl-propan-1-ol

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