(3aR,8aS)-benzyl 3a-allyl-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate

Base Information

• Chemical Name: (3aR,8aS)-benzyl 3a-allyl-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate
• CAS No.: 849360-65-2
• Molecular Formula: C₂₁H₂₁NO₃
• Molecular Weight: 335.403
• Mol file: 849360-65-2.mol

Synonyms:(3aR,8aS)-benzyl 3a-allyl-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate

Chemical Property of (3aR,8aS)-benzyl 3a-allyl-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,8aS)-benzyl 3a-allyl-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate

There total 9 articles about (3aR,8aS)-benzyl 3a-allyl-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate 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: 87.0%

(3aR,8aS)-3a-Methylsulfanylthiocarboxyoxy-2,3,3a,8a-tetrahydro-furo[2,3-b]indole-8-carboxylic acid benzyl ester (849360-64-1) + allyltributylstanane (24850-33-7) → (3aR,8aS)-benzyl 3a-allyl-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate (849360-65-2)

Guidance literature:

In benzene; Irradiation;

DOI:10.1016/j.tetlet.2005.01.016

Reference yield: 51.0%

(3aR,8aS)-benzyl 3a-bromo-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate (1580471-24-4) + allyltributylstanane (24850-33-7) → (3aR,8aS)-benzyl 3a-allyl-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate (849360-65-2)

Guidance literature:

With silver perchlorate; caesium carbonate; In dichloromethane; at -78 ℃; for 5.5h; Inert atmosphere;

DOI:10.1021/ol5004109

Reference yield:

3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1H-indole (101079-48-5) → (3aR,8aS)-benzyl 3a-allyl-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate (849360-65-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3.1: (R)-1,1'-binaphthyl-2,2'-phosphoric acid; C₁₅H₁₇F₆N₂⁽¹⁺⁾*Br₂*BF₄^(1-); 2C₁₅H₁₇F₆N₂⁽¹⁺⁾*3BF₄^(1-)*Br⁽¹⁺⁾; sodium carbonate / toluene / 2 h / 0 °C / Inert atmosphere; Enzymatic reaction

4.1: caesium carbonate; silver perchlorate / dichloromethane / 5.5 h / -78 °C / Inert atmosphere

With C₁₅H₁₇F₆N₂⁽¹⁺⁾*Br₂*BF₄^(1-); 2C₁₅H₁₇F₆N₂⁽¹⁺⁾*3BF₄^(1-)*Br⁽¹⁺⁾; tetrabutyl ammonium fluoride; (R)-1,1'-binaphthyl-2,2'-phosphoric acid; silver perchlorate; sodium hydride; sodium carbonate; caesium carbonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;

DOI:10.1021/ol5004109

upstream raw materials:

(3aR,8aS)-3a-Methylsulfanylthiocarboxyoxy-2,3,3a,8a-tetrahydro-furo[2,3-b]indole-8-carboxylic acid benzyl ester

allyltributylstanane

(3aR,8aS)-benzyl 3a-hydroxy-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate

benzyl chloroformate

Downstream raw materials:

(3aS,8aS)-3a-Methyl-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]indole

(3aS,8aS)-3a-Methylsulfanylthiocarboxyoxymethyl-2,3,3a,8a-tetrahydro-furo[2,3-b]indole-8-carboxylic acid benzyl ester

(3aS,8aS)-3a-Hydroxymethyl-2,3,3a,8a-tetrahydro-furo[2,3-b]indole-8-carboxylic acid benzyl ester

(-)-3a-methylfuroindoline